


Party of Four

by JusDim



Category: Unspecified Fandom
Genre: BDSM, Multi
Language: English
Status: In-Progress
Published: 2017-11-09
Updated: 2018-10-17
Packaged: 2019-01-31 07:48:13
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 18
Words: 32,587
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12677532
Author URL: https://archiveofourown.org/users/JusDim/pseuds/JusDim
Summary: This story is based upon real people, who have consented to being a part of this story. Their names, however, have been changed.





	1. A shocking discovery

**Author's Note:**

> This story is based upon real people, who have consented to being a part of this story. Their names, however, have been changed.

Jason was excited! His Miss had just given him permission to make arrangements to travel to this year’s FetCon, being held in Chicago. He ran into the den and logged onto the computer. The cold leather felt good against his naked body. Miss Diana had preferred him to be naked at all times at home, unless told otherwise. The harness she’d fashioned on him felt odd running up his ass crack, and the knot against his testicles didn’t help anything, either.  
His Facebook was still open as well as the page for the FetCon. “Hey stranger,” popped up a private message. It was from Annie, a lady he’d been talking to for a few weeks now.  
Jason responded. “Hi! Give me a few minutes, please.” Annie responded with a thumbs up as Jason went to the convention website. He registered himself and Miss Diana for a hotel room and slots at the con. Jason felt a rush of emotions flow through him as he clicked “Submit”. While he waited for the email confirmations to be sent, he updated his status. “Just made our arrangements for the Con next weekend!” He left it cryptic on purpose, because his parents didn’t know about his kinks. While he was forwarding the confirmations to Miss Diana, Annie had messaged him.  
“You’re going to FetCon ‘18?”  
Jason froze. He hadn’t specified what the event was. “Yes. My Miss just gave me permission to make the arrangements!”  
“We’ll be there, too,” came Annie’s reply.  
Jason had the biggest flock of butterflies form in his stomach. He was afraid of what answer he was about to get. He sucked it up, and typed out his next question to Annie. “Why are you and Seth going to a FetCon?”  
Eternity passed as Jason awaited Annie’s answer. He could feel, and even more importantly hear the stubble on his face growing. He felt his heart pounding as he watched the three little dancing dots flashing in messenger. Finally, he heard the message pop. Jason suddenly felt the color rush to his face when he read her reply.  
“I’ve wanted to go to one for years, and my Daddy finally has the chance to take me,” she said.  
“Daddy?”  
Another eternity passed before her answer came back. “I’m his middle.”

Jason stood up right away and went into the bedroom. He knelt dutifully before Miss Diana, casting his eyes downward instinctively. She looked over her pet. Diana was wearing a green bustier that hugged her cups, a black garter belt that was holding up knee-high nylons. “Speak, Puppy,” she commanded.  
Jason looked up. Miss, do you remember me telling you about Annie?”  
“Your friend on Facebook,” Miss Diana asked as she stroked his face with her foot.  
“Yes, Miss.”  
“What about her?”  
“I just learned that she’s a submissive, Miss.”  
Miss Diana planted her foot on his chest and pushed him away as she stood up. She took hold of his lead and pulled on it slightly. “Come on, Puppy.”  
Jason crawled behind his Miss on all fours. She didn’t seem upset, but she didn’t seem thrilled about this latest discovery. Thank goodness the floor was carpeted.  
Diana sat down at the computer and saw Annie sent him a new message. “Where’d you go?”  
Diana clacked at the keys. “Jason’s not here at the moment.”  
Annie didn’t send another message, which left Diana free to scroll through his chat history. Diana chuckled slightly at some of the jokes he’d made. “You’re funny, Puppy.”  
“Thank you, Miss.”  
“Stay quiet,” she said with a light thump to his head. Jason cast his eyes downward as Diana finished reading through his chat history with Annie. She stood up and took hold of his lead. “Come with me, Puppy.”

She lead him to the bedroom again. “On the bed.” Jason obediently climbed onto the bed, laying with his ass up, his face turned so that he wasn’t facing her, but he could still breathe.  
Miss Diana untied the ropes that made up his lead, and began tying him to the bed. She bound his wrists to the headboard with a pair of rope cuffs. Next, she figure 8’d his knees to her shoulders, causing his cheeks to spread open and expose his asshole. After his shoulders had been bound, she teathered his ankles to the corners of the footboard.  
She giggled as she opened the trunk at the foot of the bed and removed a metal hook that had a ball on the end of it. She showed him the hook. “Open,” she commanded. Instantly she slid the hook into his mouth and moved it around. When she removed it, she saw all the slobber he’d left on the ball. She moved back to his asshole and teased him. He wiggles slightly, but she didn’t stop him. Instead, when he was relaxed enough, the hook found itself buried inside of him. She attached the hook to the ropes that had bound his shoulders and knees.  
For the final anchor point, she used one more strand of rope to attach his swollen testicles to the footboard. She slapped his throbbing cock. “Control yourself, Puppy,” she commanded knowing full well he wasn’t that well trained. To her surprise, his cock died down slightly. “Don’t go anywhere, Puppy,” she said with a giggle. She left the room for about a minute. When she came back, she sat down on the bed next to her Jason. She stuffed a pair of her sweaty gym socks into his mouth and wrapped his jaw in tape. “Annie’s Daddy and I are going to talk.” Jason nodded as Diana teased him all night, while texting with Seth.


	2. The Revelation

**Summary for the Chapter:**

> Annie learns of an event, and makes a new friend.

**Notes for the Chapter:**

> This chapter tells “A shocking discovery” from Annie’s point of view, after a brief time jump.
> 
> This story is based upon real people, who have consented to being a part of this story. Their names, however, have been changed.

Two weeks earlier:

Annie was bored. She and Seth had just relocated to Albany, Missouri a month ago for Seth’s job, and she hadn’t been able to do much of anything. The house was organized enough, but she was in a rut. She was about to give up when she found a link on google. “FetCon ‘18” was the name of the event. She opened the link and started reading.  
She was interrupted by the door opening and closing. She put her iPad down and ran over to the door. “Welcome home, Daddy,” she said as she gave him a hug and a kiss on the cheek. She reached down and gently played with his cock. “Does this bother you, Daddy?”  
He looked down into her eyes. “Not at all, Kitten. But you should let me shower first.”  
Annie kissed him again. “Yes, Daddy. I’ll get the water started for you.”  
Seth pulled her back to him by the arm. “You will join me.”  
Annie smiled. “Anything for you, Daddy.”

She bolted for the bathroom and started the shower. The hot water always felt good, but a shower with Daddy was heavenly. By the time Annie had stripped, Seth stepped into the bathroom, as naked as she was. Annie took hold of Seth’s flaccid cock and led him into the shower. “Daddy?”  
“What is it, Kitten?”  
Annie ran the water over Seth and her’s bodies. “Daddy, since we moved here, I’ve been bored out of my mind. I didn’t mind setting up the house because it gave me something to do. But now, I wanna do something else. Maybe take a trip, just you and me.”  
Seth lathered up Annie’s hair with shampoo and expertly washed her. “What did you have in mind?”  
Annie looked up at him. “In three weeks, FetCon ‘18 will be in Chicago. I’d kinda like to go.”  
“Kitten, that’s an 8 hour drive,” Seth said, not dismissing the idea. “I’d have to think about it,” he said. She smiled as she lathered up his loofa and washed him from head to toe. She made sure to pay special attention to Seth’s cock as she washed him. Seth moaned quietly as Annie teased him. Before Seth could get too into it, she sank to her knees and finished washing his body.  
Seth lathered her loofa and stood Annie up. “Your turn,” he said. He slowly washed Annie from head to toe. He spent some time lapping at her clit. Annie held onto the walls of the shower as Seth brought her to the edge of climax and kept her there. Annie felt fireworks going off inside of her. She moaned loudly, holding onto the top of Seth’s head. Suddenly, he stopped. Annie whimpered slightly, but managed to maintain control. “Good Kitten,” he said.

After the shower, Annie went to he kitchen and start working on dinner. She was only wearing an apron. Seth walked out the door, pulling it closed behind him. A moment later, she smelled the familiar scent of a Marlboro Black. Annie had a pot of sauce warming and water boiling in another when Seth came back inside. “It smells wonderful,” he said as he kissed the top of her head. Seth grabbed a beer from the fridge and sat down at the table. He picked up Annie’s iPad and looked at the FetCon’s webpage. Seth read over the information on the screen as Annie set the table.  
After a few minutes, Annie sat down a plate of Shrimp Alfredo in front of Seth. He turned the screen off and they ate dinner. “This is good,” Seth said.  
Annie melted in her seat. “Thank you, Daddy.”  
Seth put his hand on her iPad. “I was reading over the con you would like to go to. How badly do you want to go?”  
Annie looked at him. “Daddy, I really want to do this. It would be fun to meet like minded people and see what toys and stuff people do. I’ve wanted to go to One for years, but things just weren’t right.”  
Seth looked at the iPad, then at Annie. “I’ve got some PTO coming. After dinner, I’ll give you my credit card to make the reservations.”  
Annie jumped into his lap and kissed him. “Thank you, Daddy!”

Seth volunteered to clean up from dinner, which gave Annie time to make the reservations for FetCon. A new message request on Facebook popped up. She opened messenger. “Hi. I see you like Star Trek. Would you like to talk?” “Daddy, this guy named Jason just messaged me on Facebook. He wants to talk about Trek.”  
Seth poked his head around the corner, gave her a thumbs up and a smile, then went back to work in the kitchen. After Annie made the reservations, she accepted Jason’s message.

Now:

Annie popped on Facebook to see what was going on with her friends. She checked her messenger and saw Jason was on. She dropped him a quick “Hey stranger.” She was excited to see him online. “Hi! Give me a few minutes, please.” Annie was happy. She gave him a thumbs up, then opened her newsfeed back up. She scrolled through, seeing hate posts for “The Orville” and “Star Trek: Discovery”. People were making her sick as of late. She refreshed the feed, and the top entry from Jason made her do a double take. “Is he serious,” she asked herself. “Is this possible?” She asked Jason “You’re going to FetCon ‘18?” She was excited when she saw “Yes. My Miss just gave me permission to make the arrangements!” “We’ll be there, too!” After a few moments, Jason asked why they’d be going to a FetCon. Annie told Jason about how she’d wanted to go to one for years, and how the time was right. “Daddy,” came Jason’s reply. Annie was confused. She told Jason that she was his middle. After a few minutes of nothing from Jason, she asked him where she went. Another couple of moments passed before he responded. “Jason’s not here at the moment.”

Annie froze herself. “Daddy?”  
Seth walked in and sat down with her on the couch. “What’s wrong, Kitten?”  
Annie points to her iPad. “I think I just made a mistake.” Seth takes her iPad from her and scrolls through her history, reading all the messages. Once he’s finished he hands her her iPad back. “You didn’t do anything wrong, Kitten.” Seth kissed her on the top of her head and went back to the ballgame on the TV.  
Annie looks at the iPad. “I’m assuming you’re Jason’s Miss. I’m Annie, and it’s nice to meet you,” she sent sincerely.  
After another few minutes, she received a response. Annie showed the iPad to Seth. “Daddy, Jason’s Miss wants to talk to you.”


	3. Setting Boundaries

**Summary for the Chapter:**

> Diana and Seth negotiate terms.

Diana’s phone beeped. “Seth,” was all the first message said. Diana looked down at her puppy, trussed up and anchored to the bed. She took a moment to admire her handywork. “I must say, Puppy. You look so beautiful like this.” Jason moaned into his gag. Diana gave his balls a firm squeeze. “What did you say?” Jason let out a muffled “Thank you, Miss!”  
Diana sent Seth her first message. “Did you know our submissives we’re talking?”  
After a moment, Seth replied “Yes. However, Annie just learned Jason was a sub.”  
Diana thought about that for a moment. Jason just discovered that himself. “Tell me, are you two going to the Con next weekend?”  
While she waited in his reply, she ran one of her fingernails up and down Jason’s back. He wiggled slightly in his bondage. Diana saw the slightest hint of precum forming on the top of his cock. “Mmm. Good puppy,” she said as she teased his hard throbbing shaft.  
Diana’s phone beeped again. “Yes. Are you still going after this?” Diana thought about it for a moment. Jason hadn’t exactly done anything wrong. “I suppose we are. Did you have something in mind?”

Jason kept wiggling against his bondage. The hook dug in a little harder than before. He snapped his fingers once. Diana shot a quick “Hang on” to Seth. “What is it, Puppy?”  
Jason fumbled in his ropes for the hook. “Is it the hook?” Jason nodded. Diana untied the hook from his rigging and removed it. She swore she heard Jason exhale and moan slightly in relief. “Is that better, Puppy?” She gently rubbed where the hook was pulling. He coo-ed in relief. “Would your princess plug be better?” He nodded and a muffled “Yes, Miss” was his response. She fished it out of the night table and lubed it up for him. She showed him the shininess of the plug. “On three.” She counted out to three, and penetrated him. She watched as the plug slid in easily. “Good Puppy.” She pat him on the head and looked at his hands. She watched him give her a thumb’s up.  
She picked up her phone and texted Seth. “Where were we? Ah, the con!”  
Diane shot Seth a line. “Host(ess)’s rules,” all the while teasing Jason’s cock head. She watched as Jason began leaking profusely, but she didn’t stop the torment. She slowly stroked his balls, which she swore had grown since she tied him up. “Someone’s enjoying themselves. And I think it’s you!” She swat his left cheek. He flinched and groaned slightly. Diana smiled instantly as she rubbed the spot where she’d swat him.  
Her phone beeped again. “We agree to abide by whoever’s rules. If you’re our hostess, we’ll abide by you. We expect the same in return.”  
Diana tapped out “Agreed.” She pulled up her email confirmation. “It looks like we have a suite,” she texted Seth.  
Diana slowly teased Jason’s cock again. Her phone beeped. “We have a single.”  
Diana invited them to join them in their room. “It’s your lucky day, Puppy.” She invited Seth and Annie to join them in their room when the Con wasn’t active or lively. Or, honestly whenever. Seth sent back they accepted the invite.  
Diana stood up and snapped a quick picture of Jason. “I have to tend to my Puppy now,” she texted. She sent the pic to Seth. “See you next week. Please send me your email address, and I’ll send you a copy of our rules. We can exchange safe words when we get there.” 

She sat her phone down and lubed up her hand. “You’ve done well arranging the Con, Puppy. I’m about to give you a reward.” She slowly worked her hand up and down his shaft. Jason moaned in excitement. “Huh uh, Puppy. Don't fucking cum! You won’t enjoy this if you do!” Jason whimpered into his gag while squeezing his kegals.  
Diana kissed him right under where his ball sack would droop if he were standing up. “Good Puppy.” Diana cut the tape off from around Jason’s head and pulled out the stuffing. “I want to hear the lovely sounds you make.”  
“Thank you, Miss,” he said. He turned his head to the right so he could keep breathing. Diana slow stroked his cock. “You’re behaving well, Puppy. I’m so proud of you. I expect you to tell me when you get close.”  
“Yes, Miss!”  
Diana stripped off her clothes, except for the thong she was wearing. She stroked him to frustration. She watched as he shook uncontrollably, moaning incoherently. “I’m getting close, Miss!” At that Diana stopped and stepped away. She watched and listened as Jason tried to cum, but relief was not in sight.  
Diana sat down in front of Jason’s head at the head of the bed. Luckily she was of petite build, or else such a spot wouldn’t be possible. She turned Jason’s head straight forward so that he was looking directly into her crotch. “See it. Smell it. Don’t talk. Just take it all in.” Jason took in her scent. He could smell the hormones flowing through Diana. Diana looked down at him in content. “You’re going to have fun at the con. Now, calm that cock down.”  
Jason tried like hell to relax, but found it difficult. “I should’ve known you’d be difficult right now.” She got up and pushed his head into the pillow playfully. After a couple of moments, she returned. Jason screamed out as Diana held an ice pack against his swollen cock. He tried like hell to pull away, but alas he couldn’t. His cock shriveled quickly. After he was small enough, Diana fitted him in a cs-6000 chastity device.

Once she snapped the lock, she freed her puppy. “This will keep you ready for the Con,” she said. “You’ll only be allowed freedom for cleaning, grooming, and my pleasure only.”  
Jason examined the quaint device for a moment. When he looked up at her, the pride in his eyes was unmistakable. “Thank you, Miss!”  
She made him kneel and slid off her thong. “Thank me properly, Puppy.” He wasted no time diving into the wetness between her legs. He knew exactly how to send her over the edge. She moaned loudly and held onto his head. “Yeah! That’s it, right there!” He wrote her a novel detailing his devotion on her clit and labia. Her moaning got louder and louder as she exploded on his face.  
She leaned down and kissed him hard, smearing her juices on his face. “Come on up on the bed,” she instructed. Jason climbed up on the bed, laying flat on his back. Diana gently traced his chest hair with her finger. “You do know that you’re going to have to be groomed before the Con, right?” Jason looked at her. “Yes, Miss.” She smiled. “Good. Hold me, Puppy.” Jason wrapped his arms around her, holding onto her as she held onto him. “You’ve done very good for me tonight, Puppy. I wanted you to know that.” Jason smiled. “Thank you, Miss.” She let him hold her for another hour as she trailed in and out of sleep in the last 20 minutes. She budged him. “Now go to bed, Puppy. You have a long week ahead of you.”  
“Yes, Miss.” As Diana crawled under the covers, Jason laid down on the floor, curled up in a ball. He pulled his blanket over himself and went to sleep. Diana watched him from above. “Good night, Puppy.”


	4. Biding Time

**Summary for the Chapter:**

> Seth and Annie have a little fun.

**Notes for the Chapter:**

> Special thanks to “Miss Diana” and “Annie” for their contributions to this chapter.

Seth looked at Annie. “Is there anything else you want to tell me about the Con?”  
Annie shook her head. “No, Daddy.”  
He believed her. She knew better than to lie about something like this. “You should know that I just spoke with Jason’s Miss. We are going to be their guests after the con shuts down for the night.” Annie didn’t realize she was smiling. “Diana will be sending the rules of engagement before the Con. We will be exchanging safewords, as well.” Seth had a hankering for a scene. “Annie, let’s do some role play tomorrow. Stepfather/stepdaughter.” Annie thought about it. “Ok, Daddy.” Seth walked over to her and took her hand. “Bed time, Kitten.” Annie put down her iPad and followed Seth to bed. For some reason, Annie was tired, but not sleepy. On the other hand, Seth was out like a light.

The next morning, Seth woke up at 6:45 to get ready for work. He dressed, then went outside for his first cigarette of the morning and a cup of coffee. He looked in his email and found Diana’s rules for the con.

“I try to have written rules as clean and clear as possible. I have found a simple numerical list works well.  
1\. All submissives will remove their clothing and place them neatly folded at the door.  
2\. If told, submissive will take a quick yet thorough shower.  
3\. Dominants are welcome to adorn their subs as they see fit.  
4\. Subs will stay quiet and apart as Doms discuss, and agree on, rules and hard lines. (speaking for themselves and their sub).  
5\. Submissives will follow any and all direction from every Dominant, unless it crosses a hard line or rule between sub and Owner. If a hard line or rule is crossed, the submissive’s owner will step in as needed. If a submissive wishes to make a request to another Dominant, they must go through their Dominant (Seth will speak to Diana on Annie’s behalf, and Diana will speak to Seth on Jason’s). Dominants and submissives’ pet names are exclusive to each other, and will not be used by anyone else. (Sir/boy or Ma’am/girl will be used if not speaking to your Dominant/submissive).  
6\. Safe words will be exchanged before any play commences, and honored by all. Failure to honor a safe word by any Dominant will result in the end of play for the duration of the weekend. NO EXCEPTIONS OR EXCUSES!  
7\. Have safe, sane, and consensual fun! Our submissives trust us with the gift of submission, and we must not betray that trust. “This is a generic listing of rules of engagement for the weekend.  
You may have specific rules for your sub, as I do mine. Any serious infractions during play will be dealt with by the submissive’s appropriate Dominant. As I have specific rules for my Puppy, I imagine you have a specific set for your girl.  
“Feel free to contact me with any questions, comments, or concerns.  
“Diana”

Seth studied the list of rules for a moment. “She’s thought of everything,” he said to himself. He tossed his cigarette butt into the coffee can and went back inside. Annie came downstairs like a zombie and poured herself a bowl of cereal. “Good morning, Kitten.” Annie glared up at him, then went back to her breakfast. “You ok,” he asked. She didn’t look at him. “What do you care?” He stared at her. “Look at me when I’m talking to you, Kitten.” She looked up at him. “What for, you’re not my father!” He smiled. “Starting the role play early, I see.” She smiled back. “Yes, Daddy.” Her smile disappeared. “Mom said I could go out tonight.” Seth looked at her. “Be home by midnight.” Annie looked at him again. “You can’t tell me when to come home!” Seth glared at her. “You wanna go out tonight, you’ll do as you’re told!” Annie threw her bowl in the sink. “Again, you’re not my father!” Seth grabbed his jacket and lunch and stormed out of the house. He got into his truck angrily, then smiled. “She’s good,” he said to himself. He turned the key to start his truck, but nothing happened. He let off the key and turned it again, and nothing happened. He looked over to see his head light switch was left on, probably over night. “Mother fucker!” He got out and went back to the house. “Annie, can you give me a ride to work, please?” Annie glared up at him. “Depends. Am I still going on my date?” Seth felt his face get hot. “How bout I just take your car to work?” “What if something happened here and I had to leave? Why do you need to take my car anyway, you’re just gonna park it in the parking lot for 10 hours!” Seth threw her the keys. “Fine. You drive, and keep the car!” Annie smiled, pulled on her Dallas Cowboys hoodie, and grabbed her keys. “Anytime now, old man!” She trotted out of the house and into her car. Seth was right behind her. Seth tried to rub her leg, but Annie wouldn’t have anything to do with it. She shouted “Don’t touch me, pencil dick,” alas she moved his hand off her leg. She pulled into the lot and stopped the car roughly. “Get out,” she said with a smile and a kiss. Seth got out of the car, pissed off, happy, and horny all at once.

Annie was bored at home. She looked at the time. It was 3:30 pm. She grabbed her phone. “You know, just because you stick that pencil dick in my mom doesn’t give you free reign to tell me how to live my life!” Her phone beeped. “What the fuck is with the attitude, young lady?”  
She typed out her response. “Just because you stick that disgusting thing inside my mom doesn’t mean a fucking thing to me!”  
“Is that so? We shall see when I get home from work little girl.”  
“You don’t scare me! Mom said I could go out!”  
About 20 minutes later, Annie sent him another text. “This is what I’m missing out on having to come pick your sorry ass up tonight! She and I made plans to go out and have a good time tonight...but NO! I gotta pick YOU up!” Attached to the text was a picture of Maitland Ward wearing a green t-shirt and pink panties.  
Seth shot back “Bring her with ya!”  
Annie was toying with him now. “Mom said I had to come pick you up before I can see her. Besides I asked her if she wanted to come with me, and she said FUCK NO!”  
After another few minutes, she sent Seth a pic of herself topless. “You will NEVER touch these!” The only reply he could send were three shocked emojis.

Annie received a message at 4:55. “I’m off.” She scooped up her wallet, phone, and keys and headed for her car. About a block away, she decided to be kinda reckless. She hauled ass into the parking lot, skid her tires from locking up the brakes, and blasted the horn. Seth came outside and got in the car.  
“Thank you,” he said.  
“Fuck off,” Annie responded. And with that she took off again, pedal to the metal. She was focused on being safe, yet playing her part. Seth tried to grab her leg again, but she smacked his hand. “Don’t touch me, you fucking perv!” Seth smiled kinda sheepishly. Annie pulled into the driveway. “There. You’re home. Now I’m running late for my date!” She stalked into the house and went directly for the shower.  
Seth grabbed her by the arm and spun her around. “God, I want you,” he said. His voice was full of rage and lust.  
Annie slugged at his chest. “If you want me, you’re gonna have to tie me down and take me!”  
Seth got quiet for a moment, then suddenly forced Annie into the bedroom. He pushed her the mattress, face first. She tried to fight him off, but not too hard. Seth peeled Annie out of her clothes, leaving her a naked heap. He pulled out a spool of rope and tied her wrists together behind her back. Annie pulled playfully. “You let me go or I’ll scream!”  
Seth forced her onto her knees and pulled out his throbbing cock. He expertly shoved it into her mouth as Annie mock yelled for help. He fucked her face, taking out his rage and lust on her. He stopped and bent her over the bed. “You’ve been a bad girl,” he said as he spanked her ass. She cried into her pillow as Seth pushed himself into her sopping wet pussy. Holding onto her wrists like reins, he went to town. She moaned loudly as he bottomed out inside of her. He felt himself build up! He slid out of Annie and finished on her asscheek. He scooped up his load off of her cheek as Annie turned around. She dutifully sucked his load clean off of Seth’s fingers. “I love you, Daddy.”


	5. Some Minor Discipline

**Summary for the Chapter:**

> Diana has an issue that needs immediate attention.

**Notes for the Chapter:**

> This chapter takes place three days before the convention.

Jason was tinkering with a new gag when Diana came home. He was replacing the bit out of a bit gag with a blue rubber dog bone. She cleared her throat, but Jason still didn’t hear her. She went to his phone and turned the volume up all the way. Jason jumped, pulling his earbuds out quickly, as if his ears were on fire. He looked at her, then realized she’d texted him. “Be ready when I get home.”  
“Oh, fuck!” He slowly knelt before her, casting his eyes downward in shame. “I apologize for not being ready for you, Miss.”  
She grabbed him by his hair and drug him into the bedroom. “Bend over the bed,” she commanded. He didn’t hesitate, grabbing hold of the footboard. “Stay just like that,” she instructed.

Jason pondered what could happen next. Would she beat his ass with a paddle? Would she tie him bent over the footboard and coat his balls in icy hot? Would she lube her dildo with hot sauce!? The thought of that last scenario made him whimper just thinking about it.  
Diana walked back in, holding his iPad. “Let’s see what you’ve been doing while I was gone, shall we?” She examined his home made gag. “This looks nice,” she said as she held it out completely. “Why don’t we test it out? Open!” Jason opened his mouth obediently and Diana stuck the bone into his mouth and buckled it in place. She stepped back and examined his work. “This looks well made, Puppy. Speak for me!”  
Jason let out a muffled “I don’t know what to say, Miss.”  
Diana giggled at his attempt. “This looks well made. Is it comfy?”  
Jason nodded. “Yef, Miff.”  
Diana smiled again. “The bone isn’t too big? Strap isn’t too bulky or tight?”  
He shook his head. “Nh, Miff.”  
She smiled. “You’ve done well. Is this for the Con?”  
Jason nodded again. “Yef, Miff.” Diana stepped back again. “Good Puppy. Let’s see how well it works, then.”

She laid down on the bed like a teenager, nose to nose with Jason and opened up his home screen. A quick double click of the home button revealed his recent activity: Google, messenger, Facebook, and music. “Were you talking to Annie all day?”  
Jason paused for a moment and shook his head. “Nh, Miff.”  
She held him by his chin. “You wouldn’t be lying to me, would you?”  
He shook his head. “Nh, Miff.”  
She opened messenger and checked the timestamp on the last message. 9:58am. She pat Jason on the head. “Good, Puppy. Was this gag your idea?”  
He nodded. “Yef, Miff.”  
“Where did you get the parts?”  
Jason looked up at her wide eyed, then looked at the night table, then back at her.”  
“You went into my night table without my permission???” She looked at him, fury raging in her eyes.  
He looked up at her, fear all over his eyes. He squeaked out a pethetic “Yef, Miff.”

She stood up and walked around him. “This will not do, Puppy.” Diana took his arm and led him to the kitchen. “Do not move,” she commanded as she guided him into a corner. Jason planted his nose as he waited for his Miss. He felt his cage being attached to her pathetic cock. He felt himself start to get aroused as Diana clicked the lock on the CB-6000. He whimpered slightly as next she slid a plug into his ass. He felt a slight vibrating sensation as she tested the remote control. “Perfect,” she said.  
She turned him around to face the table. “Arms our to your sides, Puppy. Hands flat and up.”   
Jason reacted instantly, not wanting to provoke her any further. He was horrified with what she did next: a box of Uncle Ben’s brown rice found a new home for it’s contents on the floor.  
Diana looked at her horrified slave. “Kneel,” she said as she pointed to the rice. He closed his eyes slightly as he assumed his new position. She cupped his chin and made him look up at her. “You’re going to stay like this while I make dinner,” she said as she made him watch her click on the plug. Almost immediately, Jason started drooling.  
He shifted slightly on his knees, trying to get as comfortable as possible with the grains digging themselves into his tight flesh. As Diana poured herself a glass of wine, Jason couldn’t help but focus on the pain he felt as the rice dug into his knees. The vibrations on his prostate increased ever so slightly, causing him to moan.  
He felt a sting on his asscheek. “Silence, Puppy! Every moan in pleasure from here on out buys you another 15 minutes!”  
“Yef, Miff,” he said. He could already tell he was drooling. As Diana tended to dinner, she turned up the plug a little more. He had to stifle his pleasure, which wasn’t hard; all he had to do was think about his knees. Instantly he was aware of the pain flowing through his legs.  
His reverie was interrupted by the sensation of suddenly getting warm. This was confirmed by the gust of hot air that accompanied the oven being opened. A pan was just put in, and then the oven was closed again. He heard a timer beeping; she was baking something!  
Miss Diana stroked the back of his head. Jason felt himself whimper slightly as he nestled his head into her hand. She gently grabbed him by his hair and held his head back up. “Soon, Puppy.” She stood in front of him, looking him over. “Look at all that drool. Pathetic,” she reached down and rubbed the head of his cock through the slit in his cage. “Precum! You aren’t enjoying this, are you,”  
He closed his eyes and shook his head. “Nh, Miff.”  
She rubbed his precum under his nose. “Bullshit.” She pushed his head back and sat down at the table. She played with the remote to his plug, turning it up slightly. “Don’t enjoy this. You’re being punished. Do you know why?”  
He nodded his head. “Yef, Miff.”  
“Do you know how upset you’ve made me?”  
He nodded his head. “Yef, Miff.”  
Diana considered her options, as she looked him over again. “Stay here,” she said with a sly smile. She stepped away for a couple of moments, only to return with a set of nipple clamps. She held them up for Jason to study. “Let’s see if you can manage to keep your composure until the timer goes off,” she taunted. He watched her as she clamped his right nipple. He groaned loudly as the clamp viciously and unyieldingly pinched him. Once he got used to it, she did the same thing to his left. And again, he groaned. She watched as it took him a moment to get used to the new sensations. She wasn’t a bit surprised that he waivered slightly, but was ultimately pleased to see he regained what composure he could.  
As she looked at the timer, she admired her handy work. She ran her hands up and down her body. She noticed Jason was just watching, as if he were mesmerized by what he saw. “Is this making MY cock hard, Puppy?”  
He nodded his head. “Yef, Miff.”  
She smiled evilly. “Too bad you’ve got that cage clamped onto you. I could really go for a good fuck right now,” she taunted. He whimpered as she teased him again. She unbuttoned her blouse and played with her tits over her bra. Jason tried to concentrate on keeping his composure. Diana ran a hand down her skirt. “Oh Puppy. It’s too bad you were naughty today. You could’ve been eating this,” she said as she lifted her skirt, displaying her shaven vag. He whimpered again, as a strand of precum flowed from him. “Naughty puppy,” she said.  
She stood up to check on dinner and the timer. “I’ll be back shortly,” she said as she stripped off her clothes in front of him. She took her clothes and left. Jason felt himself waiver again, but held on. Diana returned wearing only a T-shirt that ran down to her knees. She picked up the timer. “Are you ready for something, Puppy?”  
He nodded his head eagerly. “Yef, Miff.”  
She looked at the timer and showed it to him. “One minute until you’re finished, Puppy!”  
He straightened up quickly. He didn’t realize he’d started slouching. She grinned as she turned the timer away from him and beeped it 15 times. “You owe me 15 minutes still,” she said. Jason “frowned” behind his gag but made due. She looked at her watch then checked dinner again.  
Jason tried his hardest to maintain his composure. Time crept by like a turtle. He was surprised when the timer went off early. He looked up at Diana, who removed the nipple clamps. “Stand up, Puppy.” Jason rose, his knees popping from being bent for so long. He stretched out his legs. “Clean this rice up and after dinner, I’ll pick out any more grains that may be stuck in your knees.” He went to unbuckle his gag, and she tapped his nuts. “Not yet, Puppy. Only when dinner is served.”  
He nodded his head. “Yef, Miff.” He obediently grabbed a broom and dustpan from the pantry and swept up the rice. He couldn’t help but notice trace amounts of blood. “My god, she made me bleed,” he said to himself. Jason grabbed the swiffer mop and cleaned up the blood.

Once the rice was cleaned up, Diana had removed dinner from the oven. She let it sit for a minute before she pointed to a chair. “Sit,” she said. He dutifully sat down and looked attentively at Diana. She cupped his chin and kissed his forehead. “You bore that well, Puppy.” She sat on his lap and wiped the drool from his mouth and chin before she unbuckled the gag. He flexed his jaw. “Do you know why I made you kneel on rice?”  
He looked at her. “Mostly, Miss. I went into your nightstand without permission.”  
She looked at him. “That bit was a gift time from a very dear friend of mine, who was killed in a wreck by a drunk fucker. Angela had hoped I’d find a pet worthy of wearing it, someday.”  
Feeling the weight of that revalation, Jason fought back his tears. “And I destroyed that symbol,” he said with a cracking voice.  
She nodded. “Yes, Puppy.” He looked down at the floor, his tears flowing unbidden. Jason was a sentimental soul. He couldn’t hold back anymore, knowing he’d ruined a symbol of friendship that could never be replaced. Diana lifted him up by his chin. “Why are you crying?”  
Jason looked at her. “I didn’t realize that bit meant so much to you.” Diana kissed him gently. He looked at her, regaining his composure. “I can be gone in a week,” he told her.  
Diana felt a pang in her chest. Was she mad about the gift: yes. Did he need to be punished: yes. Does he need to go: no. She put a hand on his chest. “There’s no need for that,” she said. She picked up his home made gag. “This is amazing work. You should be proud of this, Puppy. I know Angela would be. And I feel,” she paused as she slid it into his mouth and buckled it behind his head. “You’re worthy of wearing her gag.” Jason whimpered quietly. “Fahnk yuh, Miff.” Diana kissed him on the forehead.


	6. Annie’s Road Trip

**Summary for the Chapter:**

> Seth and Annie make their way to Chicago

**Notes for the Chapter:**

> This chapter and the next take place at roughly the same time.

Annie and Seth packed their bags. They each packed one nicer outfit; Seth packed a pair of black slacks and a black and grey striped long sleeve dress shirt, and Annie a dark skirt with a low cut top. They also packed a couple of different costumes for the Con, and in a black nondescript duffle bag they packed their toys.  
“Daddy, can I assume we’re having a fancy evening out?”  
Seth looked at her. “Diana and I are taking our pets out for dinner, yes.”  
Annie rather enjoyed the thought of everyone getting familiar with each other outside of the Con. Seth nudged her and pointed to the duffle. Annie focused on packing. She threw in some toys she knew daddy would want her to take: hand and ankle cuffs, rope, a butt plug, and a suction cup dildo. Seth looked at what she packed and included a plastic bag, nipple clamps, and a roll of duct tape. Annie looked at the bag, then at Seth. “What’s in the bag, Daddy?”  
Seth looked at her. “Nothing you need to worry about yet. You may want to get some sleep. We’ve got a long drive tomorrow.”  
“Yes, Daddy.” Annie realized she wouldn’t be able to sleep tonight. Time flew since she’d met Jason online and learned about his submissive nature, let alone that he would be going to the Con, too. The butterflies flew in her stomach. “Daddy? Would you be mad if I had a nap in the car?”  
Seth leaned on the dresser. “Did you want to drive First or second?”  
Annie thought about it. “Can I drive First? I’m more comfortable with the roads on our side.”  
Seth nodded. “I’m ok with that. Once we hit Williamsburg, we’ll switch off and you can nap.”  
Annie kissed him on the cheek. “Thank you, Daddy.”

6:00 am isn’t fun. For anyone. Especially Annie. Seth’s alarm went off and instead of dragging Annie out of bed, he decided to let her sleep for a bit longer. Seth turned the shower on and started a pot of coffee. By the time he’d managed to get back upstairs, Annie had already rolled into the middle of the bed and was sprawled out. Seth looked at her phone. She was on Facebook at 2:30. “If you’re going to be pleasant this trip, I should let you get up when YOU’RE ready,” he said to himself.  
Seth’s phone beeped. He opened his text messages to see a new one from Diana. “Did you get it?” Seth texted back “Yes. It’ll fit perfectly.”  
His phone beeped again. “See you this evening. :-)”  
Seth put his phone down and got in the shower. The water was hot. He decided to make it a quick shower. By the time he got out, Annie had gotten out of bed. Seth pulled on his traveling clothes and went downstairs. Annie was wearing her bathrobe and making breakfast.  
“Good morning, Daddy,” she said as she kissed him and offered him a mug of coffee and his cigarettes.  
He took them both. “Thank you, Kitten.” He went outside and lit his first cigarette. His phone beeped again. Diana had sent him a picture of her bag of goodies she was bringing, which included rope, tape, Jason’s homemade gag, a variety of butt plugs totalling three, Jason’s cage, spanking implements, and a shock collar.  
“Shit, we overpacked,” he said ironically. He went back inside after finishing his cigarette and looked at Annie. “Is there anything else you want to bring with you, regarding toys?”  
Annie considered her options. “Do you think I’ll have a need for my strap-in?” Her eyes lit up bright at the idea.  
Seth looked at her, considering her request. “That will depend on Miss Diana and her mood. But, pack it just in case.”  
Annie kissed him on the cheek. “Thank you, Daddy.”

Three hours into the drive, Annie heard her stomach growl. Seth looked over at her. “Was that me or you?”  
Annie put her hand on her stomach. “Me. Next exit we’re gonna pull off and eat.” She looked at the clock. 11:15, which meant it was close to lunch time. Luckily for her, the Iowa City exit was coming up.  
Seth was already on google trying to find places to eat. “Follow google,” he said. He had set the GPS for “Pullman Bar & Diner”.  
Annie followed the directions precisely, and was a little disappointed about the outside of the building. However, after they stepped inside, her face lit up. It was a cozy little establishment. They sat down and looked at the menus. Annie looked merely as a formality. Seth ordered them both a Pullman Burger with fries and a Coke.  
They both admired the scenery. There was a cozy bar off in the back. The wall was adorned from top to bottom with assorted adult beverages. Their food didn’t take long to arrive, and both were drooling over their sandwiches. Annie didn’t hesitate to dive in, but Seth took a look at his plate for a moment before chowing down himself. The sandwich was amazing! Seth looked up at his lunch companion. “Take your panties off, and pass them to me up top,” he told her.  
Annie wiped off her mouth and went to the bathroom. After a couple minutes she returned, and slid her panties across the top of the table. Seth picked them up, sniffed them softly, and put them in his pocket. Annie felt herself get a little moist in her nether-regions. She went back to eating.  
After fifteen minutes of unusual silence during their refreshing lunch, their server came by with the tab. Seth looked at the check and paid the server. “No change. Thank you,” he said with a quick wink. Seth looked at Annie. “When we get back to the car, I’m going to take you in the backseat.”  
Annie felt her stomach tighten up as she finished her Coke. Seth also finished his, and they both went out to the car. Annie opened the car door, and reached inside, presenting Seth her ass. He dropped her pants and slipped a finger between her pussy lips. “Oh, you’re so wet!” He unzipped his fly and pulled out his throbbing cock. He stroked himself before pushing into Annie. “Don’t cum. This is for me,” he told her.  
She focused her breathing as Seth thrust into her. He felt her tighten her grip on him as he thrust. He pulled her panties out of his pocket and stuffed them in her mouth. Her moans were muffled as he thrust. He felt himself build up, and in no time, he shot his load inside of her.  
Seth stepped back and tucked himself back into his pants. “Have a good nap,” he said. Annie chuckled as she took her panties out of her mouth, pulled her pants back up, and stood up. She closed the back door and got into the passenger seat. As she laid back in the passenger seat, she was hot and bothered. Sleep would not come anytime soon, and she had the sneaking suspicion that wasn’t the only thing that wasn’t going to happen.

“Wake up,” Seth said. Annie somehow managed to get to sleep, but didn’t realize she slept. She raised her seat up and looked ahead.  
“Are we there, Daddy?”  
Seth nodded. “We’re here. It’s 4.”  
Annie looked at her phone, then smiled as Seth parked the car. They got out and walked into the lobby. “Have a seat while I check in, Kitten,” he instructed.  
“Yes, Daddy,” she said as she sat in a chair on the left side of the lobby.  
Seth made his way up to the front desk as a petite woman pulling her own suitcase followed by a taller man, who was also pulling a suitcase behind him, and a duffle bag slung over his shoulder, walked up to the desk. Annie couldn’t make out what was said, but he took her luggage, and sat down across the lobby from Annie. He kept his eyes cast downward as he eased himself onto the couch. She turned her attention back to Seth, who was shaking hands with the shorter woman and talking to her. They laughed as Seth waved Annie over.  
Annie walked over to them. “Annie, this is Miss Diana.”  
Annie bowed to her. “Ma’am.”  
Diana smiled. “Good girl. My puppy is over there with our bags. Come here, Puppy!”  
Jason perked up right away and made his way over to the others with his and Diana’s bags. “Yes, Miss,” he said as he cast his eyes down.  
“This is Master Seth and his girl, Annie,” Diana introduced.  
Jason kept his head down, but glanced up. “It’s an honor to meet you, sir.”  
“Likewise, boy.” Seth looked back at Diana. “Annie and I will collect our bags and meet you back down here at 6.”  
Diana looked at Jason. “Let’s take our luggage upstairs, Puppy. Once you’ve taken our bags up, report to Master Seth and help him with their bags. Then shower and get ready for dinner.”  
Jason nodded. “Yes, Miss.” He made brief eye contact with Annie, and was rewarded with a slight zap to his nuts.  
Diana took his arm. “Not yet, Puppy. You’ll both have your chances, if you behave.”  
Jason cast his eyes down. “I apologize, Miss. I apologize for looking at your sub without permission, Master Seth.”  
Seth looked at Diana. “We can manage.”  
Diana looked at Jason. “Puppy, our bags. Move!” Jason gathered his and Diana’s luggage and he followed her into the elevator. Once they were in the elevator and the doors had closed, Seth looked at Annie. “She’s awfully head strong. We’re all going to have fun this weekend.”


	7. The Voyage of Jason

**Summary for the Chapter:**

> Jason and Diana take the long way to Chicago

**Notes for the Chapter:**

> This chapter takes place almost concurrently with Chapter 6.

Tuesday afternoon

Jason loaded their luggage into the back of his Jeep. Diana took a moment to admire her puppy’s dedication. She was still trying to decide if she’d made the right decision by letting him keep his homemade gag. This long road trip would be fun!  
Jason closed the hatch on his Jeep and looked at Diana. “What is it, Miss?” Diana smiled. “Just admiring the view, Princess.” Jason felt himself tingle. “I kinda liked that Miss.” Diana shook her head. “Let’s go, Princess. We’re headed for Chicago via Logansport. From there to Champaign, and then on to Chicago.” Jason got in and set up the GPS. “May I ask why the out of the way route, Miss?” Diana grinned, as she got in the back seat.“No. Drive, Puppy.”

Jason gave her an “Alright” look, put in his sunglasses, and started driving. Diana waited until they got on the highway before she slowly unbuttoned her shirt. She wasn’t sure Jason was watching her or not, so she dropped trow totally. She was in the back seat, in the middle, wearing only a thong. She saw Jason look back in the mirror and turn his head back to the road. “Like the view, Princess,” Diana teased. Jason looked back at her as she slid her hand down her thong. Diana moaned as her fingers made contact with her clit. Jason looked back at the road and managed to keep from going into the ditch. Diana giggled. “My silly, horny Puppy,” she said as she touched herself. Diana continued to play with herself as she brought out a double ended dildo. She slowly fucked her pussy with one end as she sucked the other end. Jason was a hot mess.  
Jason pulled over the first chance he got. Diana looked up at him. “You can stop in Elkhart,” she said stifling a moan.  
Jason didn’t care. He got out of the car, opened the back door, and knelt before Diana, eyes aimed at the floorboard.  
Diana looked at him, then reached into the duffle bag, and handed him a plug. “Put this in, and I’ll ride shotgun,” she said. Diana watched as Jason got behind the wheel again. He awkwardly inserted his princess plug. As promised, Diana covered herself just enough, swapping out her double dildo for a bullet vibrator. She climbed over the seat and plopped down.

Jason started driving again. Diana played with the key around her neck. “I’m betting you’d love me to take out my aching cock right now, wouldn’t you?” Jason focused on the road. “If it would please you, Miss.” Diana reached down and rubbed his balls, which were bigger than usual. “Don’t tell me what I want to hear, Princess.” Jason nodded slowly. “I would love it if you would take out your cock, Miss.” Diana played with the key on her neck and licked his ear. “Both hands on the wheel, 10 and 2, and eyes on the road.” Jason grabbed the wheel and Diana leaned down to his crotch. She tugged gently at the zipper of his pants. It took a moment to get his cage out of his pants. “There you go, Puppy.” Jason whimpered very softly, almost inaudibly. Diana looked at him. “I took it out for you, just like you asked. It’s not my fault you weren’t specific enough,” she teased. “Focus on driving, Puppy. Once we get to Logansport, I might give you a reward.” She leaned down and kissed his swollen balls before playing with her clit with the bullet.

After what seemed like a long, cross country drive, Jason pulled into the Holiday Inn at Logansport, IN. Diana looked at him, tucking her chaste cock back into his trousers. “Let’s get a room, you dirty puppy.” They got out of the car and headed for the desk. Diana pointed to a chair in the lobby. “Sit,” she said as she continued to the desk.  
Jason sat down obediently as Diana checked in. He watched what was on TV. After about five minutes, Diana walks back to him. “Let’s go, Princess.” She hands Jason a room key and he goes after the bags. “Just the duffle bag for now, Diana yelled back. Jason felt a pang as he realized what she wanted.

Jason returned with the duffle bag and saw Diana standing by the bed. He instantly stripped naked, folding his clothes into a neat pile by the door, and crawled to Diana, keeping his eyes cast downward. Diana rubbed the top of his head.  
“Good Puppy,” she said as she considered her options. “Go sit in the chair,” she commanded as she removed his princess plug.  
Jason looked up to see which chair she meant, but when she saw the chair with the dildo suction cupped to it, he put two and two together. He lined himself up and slid onto the dildo. “Thank god I was wearing that plug for about two hours,” he thought to himself. He managed to take all of the small, unyielding rubber fallace. Diana cuffed his hands behind the back of the chair.  
“No cumming without permission. You will let me know when you’re getting close. Do you understand,” she said.  
Jason nodded, keeping his eyes down. “I understand, Miss.”  
Diana ruffled through the bag. She came back to him, covering his eyes with a blindfold. “Can you see?”  
“No, Miss.”  
Diana fumbled through the bag again and sat a bottle of lube off to the side. She gently traced down his bare chest with the key to his chastity device. “Do you know what this is, Princess?”  
Jason hitched his breath. “The key to my cage, Miss?”  
She kissed him on the lips. “Very good, Puppy.” She made her way down to the pad lock and slid the key in. Jason’s breathing got heavier as he heard her slide the key into the padlock. Once she clicked the lock open, his breathing got more intense. Suddenly, nothing was holding him back, and his cock began to grow.  
Diana slapped his balls with a wooden spoon she’d brought from home. “Control yourself, Puppy. I didn’t tell you to get hard yet!”  
Jason but his lip and tried to focus on something other than what was about to happen to him. He found that thinking about football calmed his reactions down.  
“Good Puppy,” she said as she kissed his balls where she’d slapped him. “Such a Good Puppy,” she said. She licked his dangling scrotum gently from the base of his shaft to his taint. “You’re going to have such a good time, Puppy.” She slowly stroked her cock, feeling it become fully erect in her hand. She watched his reactions as she pumped some lube into her other hand and slow stroked him, focusing on his cock head. Precum started to flow from his excited head as she slowly teased him. He moaned out loud as he pulled against his bonds. Diana smiled wickedly as she took his throbbing cock into her mouth. She sucked on him a couple of strokes before she bit down gently on him. Jason hitched in surprised as her teeth squeezed him. Diana looked up at him as she stroked him again. She could tell he was going unresponsive slightly, so she stopped. Jason took a minute to come back to his senses. “Good Puppy,” she praised him. She slowly stroked him again. This time he didn’t take nearly as long to get to the edge. He started panting. “May I please cum, Miss?”  
She grabbed ahold of his nuts and squeezed them, causing him to whine in pain from his balls being so blue. “I will tell you when you can cum,” she scolded him.  
When she let go she stopped touching him until he regained his composure. Once he was calmed again she sat on his lap, making sure not to touch her cock. “If you ask me to cum again Puppy, I will ice you down and lock you back up. Understand?”  
Jason nodded. “Yes, Miss.”  
Diana laid on her back, pulling on a pair of nylons over her feet. She gently ran her feet up and down his shaft, rubbing on the head of her cock. “Do you want to cum,” she asked him.  
“Yes, Miss!”  
“You know if you get cum on my nylons, you’re cleaning them off, right?”  
Jason considered it for a moment. “Yes, Miss.”  
She stroked him with her feet. She watched him wiggle around on the dildo in his ass he moaned. “Oh god, I’m getting close!”  
She didn’t stop. “Cum for me!” She watched as he bunched up, and right before he erupted, Diana removed all stimulation from his swollen and frustrated cock. She watched as her cock spasmed, and the cum just drooled out of his head. He groaned, still horny and hard as hell. She looked at her nylons, cum dribbled on her toes.

Diana held her foot up to Jason’s mouth. “Open,” she said. He hesitated a moment before opening. She stuck her foot, all five toes, into his mouth. “Clean my foot, Puppy! Clean it!” Jason licked the cum off her foot, gagging slightly as she crammed her foot into his mouth. She eased off and watched as Jason had less trouble. She removed the blindfold and uncuffed him from the chair. “You got some on the floor too, Puppy. Clean it!”  
Jason leaned forward and licked his spunk off the carpet. He made sure he lapped his seed up before returning to a kneel. Diana cuffed his hands behind his back again and pulled him onto the bed by his hair. “You hesitated, Puppy. Do you enjoy making me mad?”  
“No, Miss!”  
“Do you wish to anger me?”  
“No, Miss!”  
“Then why did you hesitate??”  
“I’ve never ate cum before, Miss!”  
A long silence passed between them. “Kneel, Princess.” Jason rolled off the bed and knelt before Diana, his eyes cast down. “It took a lot for you to do that today. How does it make you feel?”  
Jason thought it for a moment. “May I answer your question with a question, Miss?”  
Diana lifted his head. “Look at me and ask your question.”  
Jason looked at her. “Did making me eat my own cum please you, Miss?”  
Diana looked into his eyes. “It did.”  
Jason looked at her. “Then I suppose I’m fine with it, Miss.” Diana kissed him tenderly. “May I make a request, Miss?” Diana nodded. “Would Miss please make love to my ass?”  
Diana felt her thong soak. “In good time, Princess.”

Wednesday morning

Jason got in the shower. He was still horny as hell from last nights edging session. He’d hoped he wouldn’t be showering alone this morning. His hopes had come true. Miss Diana opened the shower curtain and showed Jason the key to his cage.

“Grab the curtain rod, Puppy,” she instructed him.  
Jason did as he was told. Thank god the floor wasn’t slippery. Miss Diana unlocked his chastity, and in no time, Jason was erect and throbbing. Diana smacked her cock a few times. “Ready for more,” she teased. Jason watched as Diana cleaned her cock, taking the time to stroke it thoroughly. Jason felt as if he might explode again.  
Diana grabbed ahold of his balls. “This is for cleaning, not pleasure.”  
Jason managed to calm down. “Yes, Miss.”  
Diana continued to slowly stroke him. She looked up at him. “You did well for me, Princess. I think you deserve a reward. After I’ve groomed you that is.” She knelt and produced a can of shaving gel and a Shick Quatro razor. She lathered his crotch and began manscaping him. “Today, we’re not going to worry about Champaign. We’re going straight to Chicago.”  
Jason nodded. “Yes, Miss.”  
Diana expertly shaved his crotch. Jason didn’t feel the need to pull or jump at her touch. “Good Puppy, Princess.”  
Jason smiled. “Thank you, Miss.”  
Diana rinsed off her cock and balls, which were still throbbing from the cleaning. Diana kissed the head and looked up at him. “No cumming without permission. If you do, I’ll make it so that it hurts to sit down!”  
Jason looked down at her. “Yes, Miss.”  
Diana took him in her mouth. She moaned quietly as she enjoyed him. “You taste so good. And clean, Princess.” She deep throated him and played with his balls. She decided to up the ante slightly and slid a finger up his ass. Jason hitched and moaned as he was penetrated.  
“That feels so good, Miss!”  
Diana smiled with his cock in her mouth, but didn’t stop. She toyed with his anus while blowing him. She could tell Jason was getting close, but wanted to see if he’d say anything.  
“Miss, I’m getting close!”  
She took him out of her mouth, but not in time. Jason came, getting it on her lips and in her hair. Diana stood up and looked at him, anger in her eyes. She squeezed his balls, bringing him to his knees. “What did I tell you?”  
Jason hugged and puffed in obvious pain. “Don’t cum....withou...OW! Without permission!”  
She looked down at him. “What did you just do?” He panted again. “I came without permission!” She squeezed his balls harder, then released him. “Get cleaned up, lock yourself back in your cage, and dry off your body, except for that white ass of yours.” She rinsed out the cum from her hair and got out of the shower. Jason had finished his shower, dried off as instructed, and crawled his way to Diana’s feet. “You need to learn Control. And you need more discipline in your life. I will teach you, Princess. Bend over the bed.” Jason did as he was instructed. Diana cuffed his wrists to the bottom of the footboard. She decided to be evil and gagged him with his homemade gag. She stepped back and admired his naked, wet ass in the air. “I’m going to spank you three times, Princess. You will count them out loud, and you will be clear when counting. If I can’t understand you, that swat will not count, and you’ll start over at one.” Jason tried to swallow, but succeeded only in drooling. “Yef, Miff.” Diana swatted him once. He hitched. “Hmm, Miff!” “That didn’t count. Start over!” She seat him again, and he yelled. “Hun, Miff!” She smiled and swat him again. “Tew, Miff!” She swat him again, this time bringing tears to his eyes and causing him to sob. “Ree, Miff!” “Start over!” She swat him again, and again he sobbed. “Hun, Miff!” She took another swing. He had to sniff before calling “Tew, Miff!” She pulled back and let him have it. He cried loudly this time. “Free, Miff!” Diana put the paddle down in front of him and unbuckled his gag. She knelt beside him on the floor. “Do you know why I spanked you, Princess?” Jason blinked away his tears. “Because I came without permission, Miss.” She nodded. “And What did I instruct you to do?” He sniffed again. “Don’t cum without permission, Miss.” She rubbed his head. “Are you going to disobey me like that again, Princess?” He sniffed. “I will do my best, Miss.” “An honest answer.” She smiled. “I admire honesty. I’m going to take a shower. Hopefully you’ll think about how much you’ve disappointed me this morning, Puppy.” An hour later, Jason was loading the bags into the car while Diana checked out of the hotel. She watched as Jason tried to sit down behind the wheel. Jason seemed to hesitate as he sat down. “Would you like me to drive, Princess,” she asked as she walked up to the car. Jason bluffed her. “I can manage.” Diana shook his head. “Bullshit. I’m driving,” she said as she took his keys. Jason nodded and got into the car. He laid on his side, being careful not to put too much weight on his ass. He was just relieved Diana hadn’t felt it necessary to plug him. Jason and Diana had checked into the hotel in Chicago. They had just met Annie and Seth in the lobby, and were making their way up to their room. Jason had erred by looking up at Annie, and Diana was going to make sure he didn’t do it again. Once the elevator doors closed, Diana grabbed his nuts. He was feeling rather tender in his scrotum right about now. “Pull another stunt like that again, and you’ll spend this convention chained to the bed.” Jason held onto the railing in the elevator as Diana released him. “Yes, Miss!” Diana rubbed the top of his head. “I know you’re excited to meet your friend. I’m going to speak with Master Seth. As far as I’m concerned tonight is kind of a free for all for dinner. Four people hanging out, breaking bread, and having a good time.” Diana pulled her phone out and sent Seth a text. A couple of minutes later, her phone beeped. Seth agreed. Diana put her hand on his shoulder. “Let’s get up here and change clothes. We’ve got a double date to get ready for,” she said with a smile.


	8. Guess Who’s Coming To Dinner

**Summary for the Chapter:**

> The Dominants treat their submissives to dinner.

**Notes for the Chapter:**

> I’ve always wanted to use this title ever since “Star Trek VI” came out!

Jason followed Diana into their room. He sat the bags down on the floor next to the bed and began to undress. Diana took a moment to look over their rather spacious accommodations before looking back at Jason. He had just finished folding his clothes and was kneeling.  
“Come here, Princess,” she commanded. Jason crawled over to her and perched by her feet, casting his eyes downward. Diana lifted his head by the chin and looked into his eyes. “We don’t have a lot of time right now. We’re meeting Seth and Annie in the lobby in an hour. We’re going to shower quickly. If you’re good at dinner, maybe there will be some playtime this evening.”  
Jason looked at her. “Will Annie and I be permitted to talk to each other at dinner, Miss?”  
Diana smiled. “Seth and I actually talked about it. This is a ‘free for all’, of sorts. I expect you to still be respectful, knowing your role so to speak, but protocol is somewhat lax. You’re free to address each other, however you WILL keep it family friendly. Do you understand, Princess?”  
Jason nodded. “Yes, Miss. Thank you.”  
Diana tilted her head. “For what?”  
Jason smiled. “For the weekend.”  
Diana kissed Jason’s forehead. “Shower. Now, you dirty dog.” Diana made her way to the shower. Jason crawled to the shower and turned on the water. He started to get in, but Diana put her hand on his shoulder. “Not yet, Princess. Kneel beside the shower. You will join me when I say so, and not a moment before.”  
Jason obediently watched as Diana got in the shower. Diana ran her hands through her hair as Jason helplessly watched her. He dared not speak, as he knew the privilege he was being given. Diana slowly lathered herself up. As she soaped up her petite body, she looked down to see Jason swelling in his cage. “You like what you see, Princess?”  
Jason poked up her grinning. “Yes, Miss.”  
Diana smiled as she slid her fingers between her labia. She moaned at her own touch, which instantly caused Jason to leak a nice strand of precum. “If you think this is bad now, wait until I let you in the shower.” She continued to touch herself.  
After what seemed like an eternity to Jason, Diana brought him into the shower. “Curtain rod,” she said. Jason reached his hands up reflexively. Diana teased his package by taking her time with the key to the padlock. Diana looked at the clock before unlocking him. “Do not let go.”  
Jason smiled, remembering the last time they were in a hotel shower together. As Diana removed the cage, her cock sprung to life. She looked at it, kissing it on the tip. “Hold still,” she said as she lathered him up. “Give me one arm at a time,” she told him. Left arm first, she washed his body from top to bottom, as usual. She teased Jason’s asshole while washing him. She grinned as he whimpered quietly. She looked up at him. “Not yet, Puppy. Good things come to good, patient boys.” Jason but his lip as she scrubbed her way down his legs, saving his crotch for the end. Jason giggled slightly as she worked the soles of his feet. “I’ll have to remember that,” she teased him. On her way back up, she pulled him down gently to her eye level. “I need you good and desperate, Princess.” She made him stand and grab the shower curtain rod again as she slow stroked him again. Jason felt himself turning into putty under her care. She slid a finger in his ass again, making him moan. “I’m getting close, Miss!” Diana slowly removed her finger from his ass and let go of her crimson red cock. “Hold that curtain rod,” she commanded. Jason fought the urge to grab her cock. Once he calmed down, she kissed the tip and turned the cold water on in the shower. He shrank rapidly as the water took effect.

Twenty minutes later, Jason and Diana got out of the elevator and walked into the lobby. Jason walked awkwardly, as he’d been fitted with a new chastity belt: this belt had a tube for Diana’s cock, a metal cup for her balls, and an anal plug. Seth stood up and shook Diana’s hand. “Good evening, Diana.” He looked at Jason. “Hello, boy.”  
Jason kept his eyes down. “Good evening, sir.”  
Diana looked at Annie. “Have you been a good girl today?”  
Annie looked at her. “Yes, ma’am.”  
Seth looked at the group. “Shall we go?”  
Diana looked at Jason with a smile. “I hope you don’t mind, but we’re going to the Hard Rock Casino here.”  
Jason looked up in excitement, realized he shouldn’t have done that and looks back down. “Thank you, Miss. Shall a I drive?”  
Diana pat him on the head. “Of course, Puppy.”  
Jason took out his keys and led the way to his Jeep. He opened the shotgun door for Diana. Once she was in, he shut the door and got behind the wheel. Diana had set up the GPS. Diana had seen Jason’s Hard Rock collection of shirts and glasses when she took him in. He’d been to several different cafes in different countries.  
Diana looked back at Seth. “Is Annie wearing the item?”  
Seth nodded. “She is. I had some trouble getting her tits into that top, but she’s secured.”  
Diana grinned and looked back at Jason. “You two are going to have so much fun tonight.”  
Jason tugged at his collar slightly as he followed the GPS.

The four of them were seated at a booth near the center of the cafe. Annie and Jason were sitting beside the wall as Seth and Diana looked through the menus. Seth ordered a cold beer for himself and a coke for Annie, while Diana ordered a hurricane, and Jason had a Dr. Pepper.  
Diana looked at Seth. “Did you tell Annie about dinner rules?”  
Seth shook his head. “Annie was being a bit of a brat in the room after our shower. I had to discipline her, and she is on a time out until after the appetizer.”  
Diana looked at Jason. “I guess you’re on a time out, too. Support your fellow submissive, Princess.”  
Jason looked down at the table. “Yes, Miss.”  
Diana and Seth looked over the menu as the server came by. The server was a little taller than Seth, dark hair, and had about 3 days worth of growth on his face. He wore a nametag that said “Tristan”. Diana slipped him a piece of paper after ordering the Jumbo Combo.  
“Have you ever been to one of these conventions, Seth,” Diana asked.  
He set his beer down, shaking his head. “Never have. I know Annie wanted to for a while, but that slug Bill didn’t pay any attention to her.”  
Diana shook her head. “That’s a shame, too. I’d have beat his ass, but that’s the Domme in me,” she giggled.  
Tristan brought the combo back and Seth looked at Annie. “Time out is over.”  
Annie kissed him on the cheek. “Thank you, Daddy. I’m sorry I misbehaved.”  
Diana pat Jason on the shoulder. “Ok, Puppy.”  
Jason and Annie looked at each other. Annie broke the ice. “Have you seen Discovery yet?”  
Jason shook his head. “Only a couple here and there. I can’t really get into it. I much prefer “The Orville.”

The couples laughed at jokes and stories they had all swapped. As Tristan came by with the bill, he looked at Diana. “I’m in,” he said.  
Diana smiled. “You know where to find us,” she said as she gave the server her credit card. She looked at Seth as he passed the man some cash. “No change.” The server nodded and left the area.  
Diana looked at Jason. “What is it, Puppy?”  
Jason scratched his head. “What exactly is our server in for?”  
Diana grabbed ahold of his head and pulled him close to her. “Tomorrow night, he will be joining us after the convention festivities for some play time.” Jason gulped, then looked at Annie. Annie grinned slightly as Jason looked back at Diana. “You don’t mind, I trust.”  
Jason looked at her. “Whatever pleases you, Miss.”  
Diana kissed his cheek. “I’ll remember you said that.”  
Tristan came back with Diana’s card. She signed the receipt and left him a generous tip. They all stood up and headed for the car. All Jason could think about was what Diana had in mind for him and Tristan. He didn’t pay attention to the conversation, but drove back to the hotel.

While waiting for the elevator, Diana looked at Seth. “Would you two like to come up to our room for a night cap,” Diana asked.  
Seth nodded. “We’d like that.”  
They all rode up the elevator. “Remember the rules,” Diana said. “They go into play as soon as you cross the threshold.”  
Jason felt himself swell in his belt. The elevator dinged and they all got off and walked to Diana’s room. The walk seemed to take forever. Diana clicked open the door, Dominants walk over to the table, and the submissives strip down. Jason managed to sneak a peek at Annie. She was wearing a chastity belt similar to his, with an added top containing her boobs. Jason shuddered as they made their way to the bar. Annie took Seth a beer as Jason made Diana a rum and coke. Jason also placed a bowl of pretzels on the tray and made his way over to them. He knelt and offered her the contents of the tray. “Is there anything I can do for you two to make your evening more pleasurable,” Jason asked.  
Diana looked at him. “Rub my feet, Princess. And bring the roll of tape.”  
Jason dutifully backed up and grabbed the lotion that Diana had packed. He slid the roll of tape onto his wrist as he crawled back to them. He placed the tape on the table as he lubed his hands up with the lotion. Seth watched as Jason rubbed Diana’s feet, then looked at Annie. “I could go for a foot rub too, Kitten.” “Yes, Daddy,” Annie responded and kissed him on the cheek. Annie slid off Seth’s shoes and slowly rubbed his feet too. Diana looked at Seth. “So how long have you and Annie been together?” Seth looked at her, taking a sip of his drink. “We’ve been physically together for about 4 months or so. But we’ve known each other going on 10 years.” Diana smiled. “That sounds like us. Except Jason came into my life about 8 months ago. He hit hard times, so I took him in about a month ago.” Diana caught Jason looking up slightly. “No drink, but stop for a moment.” She wiggled out of her thong and stuffed it into his mouth. She tore off a few strips of tape and layered his mouth. “You were good tonight. You’ve earned this.” He muffled out “Thank you, Miss.” She giggled at his problem speaking clearly. He finished with her feet and watched as Seth took the opportunity to gag Annie in like fashion, using his socks instead. “Princess, you and Annie are free to go play some cards until we get back. Do not remove your gags unless it’s for health reasons.” Seth nodded at Annie, then both Annie and Jason nodded to Diana.

Diana kissed Jason on the forehead as Jason shuffled the cards, and she and Seth wondered down to the lobby.  
Jason wrote out on a notepad. “Gin?”  
Annie nodded and giggled under her gag.  
Jason dealt out the cards. After the first hand, Annie looked back at the door and removed her gag. Jason looked at her wide eyed as she pulled out her socks.  
Annie flexed her jaw. “What are you worried about? Punishment? It might be worth it!”  
Jason looked back at the door, then removed his own gag and flexed his jaw. He looked at her. “It might be worth it, indeed. Besides, we started to choke. She never said to re-gag ourselves when we were out of danger.”  
Annie giggled. “I like the way you think!” Jason smiled and dealt another hand. Annie looked at him. “Do you want to kiss me?”  
Jason put the cards down and looked at her. “I do. But we don’t have permission. And I just got in trouble the other day for cumming without permission.” He turned over and showed her the subdued bruises from the spanking.  
Annie hissed. “Ooo! That had to hurt!”  
Jason smiled as he turned back over. “It didn’t feel good. I actually couldn’t drive here today.”  
Annie turned him over and kissed his bruised cheeks.  
Jason turned back over to face her, and returned the favor on her cheek. Annie took hold of his cheek and kissed him on the lips. Jason opened his mouth slightly, letting her tongue in. Their tongues explored each other’s mouths.  
Their kissing didn’t last long. Jason pushed her away when he heard Diana fiddling with the lock. They picked up their cards again. Diana and Seth walked into the room and looked at their subs. Diana broke the silence first. “Please tell me you both started having trouble.” Jason crawled over to her. “Miss, I started choking slightly.” Seth looked at Annie. It didn’t take her long to turn into a brat. “I just wanted to take mine off,” she said with a wicked smile. Diana examined Jason. “Why didn’t you put your gag back on when you were good to go again?” Jason looked at her. “You never said I had to, Miss.” Diana went to say something, but realized he wasn’t wrong. She looked at the clock, and then at Seth. It was only 11:45pm. “You two stay here,” Diana said. She and Seth stepped out of the room. A couple of minutes later, they came back in, an evil look on Diana’s face. “I want to play a game.”

Jason was bound and gagged on his knees. He was allowed to kneel on the bed. Diana was on the bed next to him. In front of him, Annie was also bound in a kneeling position, only she wasn’t gagged. Diana began. “You two want to have fun? Here’s the game. Annie has five minutes to make Jason cum using only her mouth. Here’s the catch: Jason is NOT allowed to cum. If he cums, Annie WILL ruin it! The winner gets to watch the loser get punished.  
Jason whimpered slightly as Annie moved closer to him. Seth held the watch. “Ready? Go!”  
Annie took Jason into her mouth slowly. She flicked his head lightly with her tongue. Jason focused his breathing. Diana held onto Jason’s body as he tried not to blast his load. Annie sucked on Jason’s needy cock, taking it deeply into her throat. Jason groaned.  
“Hold it! Don’t you fucking cum,” Diana warned him.  
Jason fought to hold back, but after a minute he groaned loudly. Annie felt him swell up in her mouth, and let go. She watched as Jason’s load oozed from the tip of Diana’s cock. Annie obediently caught all of the load as Seth stopped the watch.  
“1:02.”  
Diana glared at Jason as she ripped his gag off. “You’re gonna eat that load before I beat your ass!”  
Annie stood up and kissed Jason, pushing his cum into his mouth. Jason shuddered slightly as his cum went down his throat. Diana squeezed his cheeks. “Good Puppy, but I didn’t give you permission to cum.”  
She turned Jason over onto his stomach as Annie knelt beside Seth, proud of herself.  
Out of the dufflebag, Diana took out her paddle. For Jason, the paddle had a dog paw cut into it. “This will hurt me more than it will you, Puppy.” Diana spanked Jason. He flinched and groaned loudly as the paddle ripples across his white ass cheeks.  
Annie felt herself get a little wet, and whimpered slightly. Seth looked down at her immediately. “You want some too, Kitten?”  
“No, Daddy,” she said.  
“I think you do,” Seth said. He stood her up and bent her over the bed, across from Jason.  
Diana watched. “Ooo! You two can look into each other’s eyes as you both get beat!”  
Seth took off his belt and began spanking Annie, as Diana continued with Jason. Both subs spent the next 20 minutes getting red asses.


	9. The First Morning, part 1

**Summary for the Chapter:**

> The couples partake of the first day of the Con.

Jason woke up to Diana holding a tray of food for them. “Good morning, Princess.”  
Jason stretched in the bed and sat up. “Good morning, Miss.” He crawled over to the table and knelt besides Diana. She cut up the scrambled eggs she’d ordered for Jason and fed him by hand.  
“How’s your ass, Puppy?”  
Jason winced slightly as he remembered last night’s brutal spanking. “Still a little sore, Miss.”  
Diana fed Jason another serving of eggs as she looked back at the paw prints across his cheeks. “Will you be able to hang today?”  
Jason rubbed his cheeks gently. “I believe so, Miss.”  
Diana turned in her chair and looked at him as she gave him a slice of bacon to eat. “Puppy, I don’t know if you’ve ever been to one of these cons before or not. There are a lot of things that happen here. If you’ve got some demonstrations or mingling you want to take part in, I will be there with you.” She gave Jason a small swig if juice.  
Jason rinsed his mouth and swallowed the juice mix. “I’ve never been. But I know this is something you’ve wanted to do for a while, too. I’m just looking to have a nice, long weekend away with you, Miss.”  
Diana pat his head. “Good Puppy. You will be caged, plugged, and on my lead. Unfortunately you can’t be naked. I suppose that’s somewhat of a mixed blessing.” Jason smiled as she continued. “We’ll see what’s planned for the weekend here, and see what can be done. I know I’d like to partake in a rope work demonstration with you.”  
“Thank you, Miss. I’m honored you wanted to do this with me.”  
Diana pat his head as he laid his head on her leg. “Once we’ve finished breakfast, we’ll scout it out. This early, there won’t be too many people around.”

Jason stood up to leave, but Diana put her hand on his shoulder. “Not yet, Puppy. I want you to do something for me first. Kneel.” As Jason obediently knelt before her, Diana took out a small baggy out of her suitcase. “This is not a punishment, Princess.” Jason watched as she knelt with him. “Anything for you, Miss.” Diana licked his lips and made a circle of clothes pins on Jason’s nut sack. Jason shifted slightly as Diana watched him. “Is that hurting, Puppy?” Jason made eye contact with her. “No, Miss.” Diana grinned evilly. “It will. Will you wear these for me for about a half hour or so, Princess?” Jason looked at her. “If it will please you, Miss.” Diana pat him on the head. “Good boy,” she said. She snapped a picture of Jason’s sack and sent it to Seth with the caption “Top this.” He watched as Diana grabbed the ice bucket from the room and headed for the door. “Watch some TV until I get back, Princess. You’ll feel some tingling here in a few minutes. This is perfectly normal. Don’t touch the clips. Do you understand?” “Yes, Miss,” he said. Diana kissed him and looked him in the eye as she held his chin. “You’re making me proud, my needy puppy.” She left Jason in the room to enjoy some time alone.  
Jason clicked “Today” on the TV and laid back on the bed. He felt fine until about ten minutes in. He felt a tingling start to ripple across his sack. It was a weird sensation. Another ten minutes passed and the tingling had become a stinging. Jason started to shift a lot on the bed. He considered shifting the clothespins, but thought better of it.  
After 35 minutes, Diana returned with the bucket in hand. “How are you feeling, Princess?” Jason looked up at her. “This is starting to hurt now, Miss!” Diana smiled. “I know.” She looked over her handiwork. “Would you like to see what your friend Annie is doing right now?” Jason looked at her. “Yes, Miss.” Diana showed Jason a picture of Annie. She was naked, her arms were tied behind her back, and those were rigged up over the bar in the closet. She had a clothes hanger clipped to her nipples, which was tied to her wrists. Her mouth was wrapped with duct tape. Diana looked to see Jason’s pathetic dick was getting hard. “Are you enjoying this, Puppy?” Jason smiled slightly. “Which part, Miss?” Diana smiled. “All of it.” Jason looked at her. “Would I be in trouble if I said I was?” Diana shook her head. “No. But I have something for you. Move to the chair.” Jason fell to the floor and crawled over to the chair, which still had the dildo attached to it. Diana stopped him from sitting long enough to put a condom over it. She instructed her puppy to lube his asshole before sliding onto the seat. She cuffed his wrists behind his back and slid a blindfold over his eyes. He felt her toying with the clips in his sack. Each one she played with lit that part of him up. She kissed the head of his swollen cock. “Be glad I didn’t clip this, Puppy.” He whimpered slightly as she removed the clips two at a time. Jason thought that he’d feel relief when the clips came off, but for some reason he felt a different kind of pain. He felt the last clip removed, then suddenly a very cold sensation. He squirmed, which made the dildo in his ass rub against his prostate. Diana watched as he leaked precum. “That’s a good boy,” she said. After a minute that felt like ten, Jason felt a warmer sensation on his sack, followed by an up and down movement on the seam. He couldn’t help but moan.

Diana removed the blindfold and looked him in the eyes. She pointed to the bucket of ice, then to her tongue. “That’s what you were feeling, Puppy.” She kissed him, slipping her tongue inside his mouth. He dared to touch tongue tips with her, which was met with her holding onto his head. As they kissed, Diana ground herself on Jason’s throbbing cock. He felt himself getting close, and Diana could tell. She pushed herself off of him, and watched as his cock danced. To her relief, he didn’t orgasm. She waited until he had calmed down again before she warmed up his sack with her mouth again, this time letting him watch as she carefully sucked on his balls. She edged him three more times before icing his cock down and locking it in his cage, and unlocking the cuffs. “Get in the shower and wash your body. Call for me when you’ve washed everything except for my cock.” “Yes, Miss,” came his dutiful reply as he slid off of the chair and went to the bathroom.

Jason had finished washing his body, except for Miss Diana’s cock. “I’m finished, Miss,” he shouted. Almost instantly, the shower curtain slid open and in stepped Diana. She looked him over.  
“Good puppy,” she said as she looked up at him. “Curtain rod,” she commanded. Instantly he took hold and she came up behind him. “A little fun before we finish,” she said. He felt the water run between his ass cheeks as she rinsed him out. Then he felt his cheeks being spread and a licking sensation on his hole. He squirmed slightly, caught by surprise. He couldn’t help but coo quietly. He felt a finger and the unmistakable sensation of lube circling his hole. “Relax, princess,” she said.  
Jason exhaled as he felt something slide inside of him. As he felt a slight pulling sensation, he knew it was her finger. She held it there. “Show me what you need,” she told him.  
Slowly Jason rocked himself on her finger. He couldn’t help but moan as he felt a wave build up inside of him. He squeezed his body in an effort to keep from erupting, but felt her hand slide from his ass. He whimpered slightly as his body came down from his edge.  
Diana finished washing off her hand and turned off the water. She watched as Jason continued to hold onto the curtain rod. She ran her index finger over the head of his caged cock, collecting the strand of precum from his cock and smeared it onto his lips like lip gloss.  
“Such a beautiful puppy,” Diana complimented him as she prepared him for the event.


	10. The First Morning, Part 2

**Summary for the Chapter:**

> The convention begins

Annie finished adjusting her school girl costume as Seth threw on jeans and a t-shirt. He looked her over and put a black choker around her neck. He examined her, keeping a strand of rope in his pocket...just in case. “Ready to go downstairs,” Seth asked.  
“Whenever you are, Daddy,” she answered.  
He led the way outside the room and down the hall to the elevator. On their way Seth knocked on Diana’s door to let them know they were headed down.  
A couple minutes later, Diana and Jason met them in the lobby: Diana was wearing a jogging suit and Jason was wearing a pair of jeans, and his dog toy gag around his neck. The ass was ripped out of the jeans to reveal a dog tail butt plug. Jason had been having some troubles with his knees, which had been resurfaced by his time after the grits. As a result, Diana allowed him to stand and walk like a human, however whenever he wasn’t walking, his head and eyes were aimed at the floor.  
“Good morning, Seth,” Diana said.  
“Hello,” Seth responded. “Taking your puppy for a walk?”  
Diana grinned back at Seth. “Puppy had a bad night last night. So I’m taking him downstairs to look around.”  
Seth couldn’t help but chuckle, “Would you like to join us for lunch today?”  
Diana cocked her head. “We’d love to!”  
The elevator arrived, and Diana led Jason into the elevator by his rope leash.  
Annie looked at Jason, then at Seth. “Can I pet her dog?”  
Seth looked at Diana who was already looking back at her. “Sure. He’s a friendly, playful puppy. He won’t bite you, if he knows what’s good for him.” Diana pointed to the floor, which was Jason’s cue to kneel.  
Annie stepped over to him, knelt, and softly stroked the top of his head. Jason knelt and held still as Annie rubbed his belly. Jason couldn’t help but quietly moan in response. He rolled over onto his back, holding his arms and legs like a dog would. Annie giggled and stopped as the elevator came to a stop at the lobby. “Thank you,” she said.

Jason stood back up as the doors opened. He was amazed at what he saw. There were hundreds of men and women buzzing around the lobby. Diana led him out of the elevator and stopped at the door.  
“If you misbehave, not only am I going to gag you, but you’ll be punished later. Do you understand,” she asked him.  
“Yes, Miss,” he answered back.  
Jason looked over in time to see Seth finish tying Annie’s wrists together in front of her, leaving enough length of rope to use as a lead. Diana led Jason into the auditorium and sat down in a chair next to the aisle. She signaled him to sit down as Seth and Annie sat down behind them.

A middle aged woman with cropped brown hair, wearing a business suit approached the podium. “Ladies and gentlemen, and anyone in between, welcome to the 15th annual Chicago FetCon. I’m your hostess, Mistress Eva Notty. My rules are simple: behave in a civilized manner that won’t get us kicked out, and we’ll be able to keep doing this. Pet owners please make sure your pets don’t have any accidents. If they do, make sure it gets cleaned up.”  
Jason looked up at Diana, who was scratching the nape of his neck. He felt his cage starting to get tighter.  
Eva continued. “We have a lot going on this weekend, including rope demonstrations, couples costume contests, vendors from across the country, and we have rooms available should anyone wish to collar their submissives. That being said, have fun, and enjoy yourselves!”

All the dominants in the room started clapping. Jason looked up at Diana. “Collar?”  
Diana leaned down. “That’s kind of like a marriage ceremony, usually between a Dominant and submissive couple.”  
Jason looked up at her. “Kind of like us?”  
Diana jumped slightly, seeing a gleam in his eyes. “Kind of, yes.”  
Diana looked back as the first demonstration was set up, however Jason didn’t look away. In fact, after a few moments Diana looked back down at him, only to see he was still looking at her. “We’ll talk more about it later. Come on up here and have a seat.”  
Jason crawled over to the chair next to her and sat down as a cellophane demonstration was about to begin.  
Seth leaned forward. “If they ask for volunteers, I’m going to let Annie go up there.”  
Jason immediately looked at Diana, but before he could get a word out, Diana gagged him. Diana turned back to Seth. “Good to know. I may send Princess up, too.”

Jason and Annie found themselves facing each other as a rope work demonstration began. Jason’s cage became very tight and almost uncomfortable. Jason wasn’t paying attention to the instructions Diana was being given; he was just happy to have her tying him. He wasn’t really bothered about everyone gawking at him either. Diana got close to Jason’s ear. “This is making me wet, puppy.” Jason felt his locked cock leak a drop of precum. Annie raised an eyebrow as they continued. Before Annie knew it, Diana had been instructed to start binding her as well. She gave Seth a quick glance, who nodded in approval. She looked back at Diana, who was looking at her already. “I won’t hurt you intentionally...without Seth’s permission anyway,” she said with a reassuring smile. The last rope Diana tied was a long strand around the waists of her models. Annie could feel Jason’s caged member pulsating. Diana leaned into Annie. “Give him a tease,” she said quietly. Diana looked to Jason. “Control yourself.” Annie wiggled her pelvis, which caused Jason to whimper. Annie didn’t stop, making Jason extremely desperate for both release and penetration. Maybe from Diana; maybe from Annie? Maybe both? Doubtful. Jason's train of thought was interrupted by a slap to his ass. “Easy, puppy. Save some for later,” Diana commanded as she untied the models from each other. Jason knew he wanted more to do with either Annie or Diana. He didn’t care who or how.


	11. The first afternoon

**Summary for the Chapter:**

> Our friends deal with an incident before lunch.

Jason was bent over the bed in their suite. He was naked, and his wrists and ankles were tied to the footboard of the bed. He wasn’t gagged, surprisingly, but he did have clips hanging from his ball sack and the tip of his cock. He’d been like this for about 45 minutes.  
Diana looked up from her magazine, a look of disgust on her face. “Do you know why you’re trussed up like this, princess?”  
Jason nodded. “Yes, Miss.”  
Diana walked over to him and picked up the paddle as she ran her hand over the red marks already on his ass. “And why, again, are we here right now?”  
Jason gulped as he looked over at Diana. “Miss Diana, I’m bound bent over like this because I had an accident on Master Seth’s kitten.”  
Diana lifted his chin up and locked eyes with him. “What did you do?”  
Jason felt himself tear up. “I came on her outfit, Miss.”  
Diana dropped his chin. “You came on her, without permission! Like a BITCH!” At the saying if the word bitch, she spanked his red ass again, which caused him to scream in pain. She pelted his ass again ten times per cheek. She stopped to look at her phone, which had beeped because of a text from Seth. “That’s just lovely. Her blouse is stained! He’s making us replace it!” Diana resumed her assault on Jason’s ass in response to the news.  
Jason couldn’t take it anymore. His ass was throbbing, and the tingling in his junk became too much for him! He felt overwhelmed! He started to panic, and almost forgot his safe word! “RED! Red red red!”  
Diana stopped herself after hearing the second ‘red’, dropped her paddle, and started releasing Jason from his bonds and the clips. She pulled him into her on the bed and held him. “It’s ok. It’s ok, I’m here. And I’m done. Talk to me, Jason.”  
Jason wiped his eyes as he held onto her. “I’m sorry, Miss. I couldn’t take t anymore. Everything was too intense!”  
Diana kissed the top of his head and held him tightly. “It’s ok. I’m proud of you for speaking up. I’m sorry, Jason! I got a little anxious.”  
Jason cried a little more, slowly calming down. Diana cradled him, but not before she took off her clothes. They both laid on the bed together, naked. Jason finally looked up at her again. “I’m sorry about pissing off Seth, and ruining Annie’s blouse. I’m sorry I let you down.”  
Diana tilted his head up and looked into his eyes. “Clothing can be replaced, and you didn’t let me down.” Diana kissed him gently on the lips. “Take a nap, Jason. We’re going to rest for a few hours.”

Annie looked at Seth. “Daddy, are you ok?”  
Seth looked at his middle. “Not really. That fucker ruined your blouse! In front of a crowded room!”  
Annie sat in Seth’s lap and stroked his cock. “He didn’t mean to. It was an accident.”  
Seth looked at her. “I know he didn’t mean to. But he still blew his load on you.”  
Annie kissed Seth as his phone beeped. It was Diana. “We have a situation here. We won’t be joining the convention for a few hours. He safe worded. I’ll text when we’re heading back out.”  
Seth sent a text in response. “Is everyone ok?”  
After a few moments, Diana’s response came back. “We will be. You two enjoy Chicago and I’ll message you when we’re going to get back to it.”  
Annie laid her head on Seth’s shoulder. “Is everything ok?”  
Seth stroked her cheek with the back of his hand. “Yeah, it will be. Jason safeworded. They’re going to take some time to relax and join us later.”  
Annie smiled. “Oh goody. We can enjoy each other a little too, can’t we?” Annie slowly made her way to the floor and opened Seth’s trousers. Since Jason ruined her blouse, she was only wearing her skirt and nylons. She wasn’t permitted panties this morning.  
Seth adjusted himself in his chair as Annie took his manhood into her mouth. She gently scraped the head with her teeth, which made him leak slightly. Annie started drooling as she tasted the sweet flavor of precum. She moaned as she bobbed her head back and forth as she grabbed her ankles.  
Seth grasped his manhood and slowly stroked it as Annie bobbed on him. She stopped on his cock and sucked on his full balls. Seth stroked himself harder as Annie moaned. He felt himself build up. “Here we go,” he said! Annie stopped sucking his balls and opened her mouth as Seth came on her face and on her tits. She moaned as the hot fluid hit her skin.  
Once Seth was spent, she wiped up his fluids on her fingers and sucked them clean.

Three hours later, Diana returned to see Jason in bed, still asleep in the same position she’d left him in earlier. She quietly sat the bag down on the table, stripped her clothes off, and climbed into bed gently, so as not to disturb him.  
Diana slowly and gently took Jason’s cock in her hand and rubbed gently. “Jason,” she said softly.  
Jason shifted slightly as he realized someone was touching him. He looked back to see it was Diana. He rolled onto his other side and faced her. “Hello, Diana. What time is it?”  
Diana looked at the alarm clock. “3:45. Do you want to eat?”  
Jason embraced her. “Maybe once we finish this. Do I...”  
Diana cut him off. “This is part aftercare. You can enjoy this,” she said as she took him into her mouth slowly. “I hope you slept well,” she said as she sucked him.  
Jason smiled. “I slept good, but this is a good way to wake up.”  
Diana smiled. “I want you to let me know when you’re getting close,” she said.  
Jason nodded. “I’m pretty close now,” he said.  
She sucked on him a few more passes before stopping. She watched as Jason’s spunk drooled out of his manhood.  
Diana let him settle down and ruined him three more times, noticing the third time seemed to take a while. Once she felt he was ruined enough, she started to edge him. Jason wiggled around on the bed as Diana edged him for the next half hour. She leaned down on him, cheek to cheek with him. “I’m going to fuck you now. And if you feel like cumming, you can without asking.”  
Jason smiled. “I understand. Thank you.”  
Diana kissed him, allowing her tongue to gently explore his mouth. She reach down and slid her fingers into her pussy. She was sopping wet. She straddled him and slid him inside of her. She gasped at how big he was as her petite form ground on him. She felt him take ahold of her thighs. Diana took his hands and rubbed them on her bouncing tits. He squeezed them playfully as she bounced on them.  
Jason felt slightly frustrated. He felt a dull urge to cum, but that urge wasn’t strong at all. Diana continued to ride him, smiling at the look of angst on his face. “You’re right where I want you for this,” she told him as she gave him an evil smile. Jason gently kneeded her tits as her bouncing became more of a grind.  
Diana leaned down and moaned into his ear. “God, this feels good!”  
Jason reached down and thumbed Diana’s clit, catching her by surprise. She moaned loudly into his ear. He felt himself build up. “I’m gonna cum,” he shouted.  
Diana ground on him faster, rubbing him just right. Jason bucked and groaned loudly as he exploded inside of her. He moaned loudly as he pumped her full of his cum. Once Jason relaxed, Diana slid off of his cock and presented her cream pie to him. “Clean it out, puppy.”  
Jason pulled her hips closer to his face. “Yes, Miss,” he said as he obediently cleaned out his juices. The mixture of his cum and her pussy juices tasted divine.

Diana climbed off of Jason’s face after he made her cum twice. “I know I said aftercare would be finished once you got off, but that was a fib. Aftercare ends once we shower. We’ll wash each other, and I’ll rub some lotion on your ass. Then we’re going to dinner with Annie and Seth. The rules will be as relaxed as last time. At least as far as I’m concerned.” Diana indicated the bag on the table. “I took your car and went shopping. You’re going to give Annie a new blouse to replace the one you ruined.”  
Jason smiled. “Yes, Miss. I still don’t know how I was able to make a mess like that on her through the gym shorts I was wearing for the rope demonstration.”  
Diana looked at him. “The only thing I can think of is when I bumped into your plug, it hit your prostate just right and caused you to cum. You musta been hornier than we thought you were.”  
Jason smiled as he climbed into the shower. The two cleaned each other up, and before Jason was allowed to get dressed, Diana sucked Jason’s cock for a few minutes, long enough to get him throbbing again. “How do you feel?”  
Jason smiled. “Green.”  
She grinned as she brought him to the edge before locking his cock into a new device. It was a metal tube that wrapped around his cock, leaving his head exposed. It was such a tight fit that it squeezed his shaft, turning his head purple. She waited about ten minutes to see how he felt.  
“Not bad. It’s not tingling and going numb or anything,” he told her.  
Diana looked at him and palmed his head. Jason jumped at the sensation of her palm rubbing his sensitive cock head. They giggled as Diana slipped in his vibrating butt plug. She also took the precaution of slipping a condom over his cock and wrapping the end in medical tape. “Now get dressed,” she commanded.  
“Yes, Miss,” he responded.

Diana and Jason met Annie and Seth at the Hard Rock casino again. This time Diana offered to be the DD. They were seated, submissives against the wall like yesterday. Their server approached the table. It was a blonde female, who was overflowing up top.  
Jason didn’t realize he was staring at the blonde until he felt a squeeze in his balls. “What are you drinking,” asked Diana.  
Jason shook his head. “A pina colada, please.”  
Once the server took their order, Jason took out a bag and handed it to Annie. “Hey, listen. I’m sorry about earlier. Things happened just right...or just wrong...during the rope demonstration.”  
Annie took the bag and pulled out the blouse inside. “Thank you,” she said as she squeezed his hand.  
Diana looked at the diners. “If you’ll excuse me for a moment, I need to make arrangements for tonight.”  
Jason looked at her. “Arrangements?”  
“Oh, I didn’t tell you,” she feigned forgetfulness. “Hang onto that thought, puppy. I may or may not have something to tell you.” She kissed his forehead as she got up to leave. Once she was out of eyeshot, he felt his plug turn on, giving off a full vibration.  
Seth looked at Jason. “Thank you for replacing Annie’s blouse. I understand you had a rough afternoon because of it?”  
Jason looked down at his feet, then back up at Seth. “I did, actually. And if you don’t mind, I’d rather not go into fine details about it.”  
Seth nodded. “I understand. I just want you to know that I’m not pissed, rather more annoyed about the situation more than anything. But, I’ll get over it.”  
The busty blonde returned with a tray of drinks just as Diana came back to the table. Jason watched as Annie whispered something into Seth’s ear, and Seth nodded and stood up. “If you all will excuse me for a moment,” he said as he stood up and ran in the direction of the server.  
Diana looked at the two subs. “Go ahead and enjoy yourselves,” Diana told them. She looked at Jason. “Build up your strength. You’ll need it for later.”  
Jason nearly spit out his drink in surprise. “Say what?”  
Diana looked at him. “So Tristan is working tonight, and said he’s willing to come with us tonight.” Jason looked at her, not sure if he liked where this was going. Diana continued, “We’re going to play tonight, just you, him, and I.”  
Jason looked at her, feeling his face flush. “Miss...”  
Diana looked at him. “I know what you’re thinking. I’m about to check something off of your bucket list.”  
Jason looked at her, taking another drink of his beverage.


	12. Moving lines, Part I

**Summary for the Chapter:**

> Annie learns something about herself, thanks to Seth and the Waitress.

**Notes for the Chapter:**

> Moving Lines, parts I and II run concurrently.

Annie and Seth said good night to Diana and Jason. Seth was still upset with Jason over Annie’s blouse, and wanted the night to sleep it off. As Seth drove off to the hotel, he lit a cigarette. “That boy’s lucky,” Seth said.   
Annie looked at him. “Why do you say that, daddy?”  
Seth took another drag. “Diana told me that he had a bad day today. I dunno. I think I’m just upset more than anything.”  
Annie rubbed his leg. “Don’t worry about it, daddy. He made a mistake, and made it right. As far as I’m concerned, we’re ok.”  
Seth stopped at a red light. “It’s disgusting that another man came on you! I don’t want to share you with another man. Ever!” Annie looked at him stunned. “But I do have a surprise for you tonight.”  
Annie had an excited look on her face. “A surprise? What is it, daddy?”  
Seth smiled as he took another drag. “You’ll see. I don’t want to spoil anything for you.”

Annie was naked when someone knocked on the door. She was directed to kneel and wait patiently as Seth answered the door. After a moment, she was allowed to look up. She locked eyes with the waitress from the casino. Except this time, she was wearing denim shorts and a green flannel shirt, which was tied off just under her enormous rack, exposing her belly. “Daddy?”  
Seth looked at the blonde. “Go ahead and get set up,” he told Gianna as he stood above Annie. “You’d mentioned being willing to be dominated by a woman one time.”  
Annie gulped. “Daddy...I’m not sure if I’m ready.”  
Seth knelt in front of Annie. She wasn’t ready for the uncharacteristic move, but she locked eyes with him. “Annie, I’ll be right here. I won’t let anything happen to you. I promise.”  
Annie hesitated, then looked at him. “Ok, Daddy.”  
Seth kissed her as Gianna returned. Seth looked up at Gianna. “She’s all yours. I will be watching to make sure nothing happens to Annie.”  
Gianna grinned. “I’ll be sure to give you a good show, then.” Seth pulled up a chair and took a seat.

Gianna looked at Annie, sizing her up like a commodity. She smiled. “Get on all fours, girl.”  
Annie obediently assumed the new position as Gianna looked her over. Annie felt a bit self conscious about her physique, but that was all put to rest when Gianna crouched down in front of her, meeting her gaze. “Such a beautiful little girl,” she praised.  
Annie smiled. “Thank you...Miss?”  
Gianna cracked her hand on her ass. “Goddess Gianna!”  
Annie jumped and smiled. “Yes, Goddess Gianna! I’m sorry for the disrespect, Goddess Gianna!”  
Gianna smiled and looked her over again. “Good girl. Stand up.”  
Annie stood slowly as Gianna led her to the table in the room. Annie was ordered perched on the table as Gianna bound each limb to a corresponding table leg.  
Annie looked at Gianna’s handiwork, then up at Seth. He was already shifting in his seat, controlling the raging boner in his pants. Seth moved the seat closer to the table as Gianna tied a crotch rope around Annie’s waist.  
Gianna looked over her temporary toy. “God, girl. You’re making me wet already and I haven’t even touched you yet!” She reached down and touched her dripping wetness through her shorts. She slid her fingers into Annie’s mouth, offering her a taste. Gianna wasn’t expecting Annie to be so compliant.  
Annie looked up at her. “You taste so sweet, Goddess Giana!”  
Gianna looked at her. “Try the real thing,” she said as she slid off her bottoms and grabbed ahold of Annie’s hair. Gianna drove her head into her bare pussy. Seth moved his seat so he could watch as Annie lapped at her, gently scraping Gianna’s clit with her teeth. Gianna moaned and ground against Annie’s face. Gianna felt herself build up. She moaned louder as she exploded on Annie’s face.  
Seth was touching himself over his jeans when Gianna looked over at him. She looked at Annie. “I’ll bet you wish you could help him, don’t you, girl?”  
“Yes, Goddess Gianna.”  
Gianna grinned evilly. “Too bad you’re bound to that table. He does look kinda hot, though.” She walked over to Seth and took him by the hand. She led him over in front of Annie as she kissed him. Annie felt herself starting to get pissed and turned on at the same time.  
Gianna knelt in front of Seth, kissing at the bulge in his pants. As she slid his pants down, his manhood sprung out of his drawers, slapping Gianna in the face. “I think someone needs some attention,” she said as she took his tip into her mouth. Gianna glanced at Annie and winked as she serviced Seth. Gianna bobbed on him for a few minutes, removing her top. She felt him building up some precum before she looked over at Annie. “Don’t worry, I won’t let him cum...yet.”

Gianna sat Seth down in front of Annie and walked over to her bag. Annie and Seth exchanged a silent glance. Annie was smiling as Gianna came back to her. Gianna kissed Annie, driving her tongue into her mouth. Both women moaned during the kiss.  
Gianna held up a double dildo gag, one end long and one end stubby. Gianna slid the longs end into Annie’s mouth to lube it up. Annie moaned as Gianna forced the phallus in and out of her mouth. “That’s a good girl. Get it good and wet,” she said.  
Annie drooled and slurped on the dildo. As Gianna slid it out to examine it, she looked at Annie. “Good girl.” Gianna slid the stubby end into her mouth and buckled the gag in place. Gianna walked around Annie.  
“Look at that ass!” Gianna swatted her, making Annie yelp. Annie’s pussy started leaking in anticipation. Gianna lapped at her juices, causing her to moan. She looked up at Seth. “Enjoy the show, stud.”  
Gianna made her way in front of Annie and cupped her chin. “You’re gonna make me cum with your face.”  
As Annie nodded in understanding, Gianna slid the tool inside her and rode her face. Gianna moaned as she ground into Annie’s face. As she motioned Seth over, she rubbed her clit. Gianna slid Seth’s tip into her mouth, still moaning.  
As Gianna bobbed back and forth, building herself up, she stopped sucking Seth off and pointed back behind her. Seth went behind Annie and lapped at her. Both Gianna and Annie moaned in their own pleasures.  
Gianna slammed into Annie, grinding hard on the dildo. She moaned loudly as she exploded, leaving a puddle on the floor. Gianna looked back at Seth as she removed Annie’s gag. “I’ve got one more goody for the both of you,” Gianna said. She reached into her bag and slid on her strapless strap on. “Suck it,” she ordered.  
Annie took it into her mouth, lubing it up good as Seth drilled her from behind. Gianna looked up at him. “Where do you wanna nut?” Seth raised his head slightly. “In her mouth.”  
Gianna looked down at Annie and then back up at Seth. “I think I’m ready too,” she said as she went for Annie’s backside. Gianna and Seth high fived and Seth went up front.  
Gianna slid her dildo inside of Annie and pumped into her. Before Annie could object, she felt a wave of pleasure flowing through her. One cock to please, and one to enjoy. Annie moaned loudly. Before she knew it, she felt an uncontrollable urge to push. She heard what sounded like water being poured onto the table.  
Annie looked down, then back at Seth as Gianna slid out of her. Seth kept ahold of Annie’s head as he bucked and shot his load down her throat.  
Annie choked slightly at the power behind the load as she swallowed it whole. After Seth slid out of Annie’s mouth, he looked at Gianna. “Let her go,” he instructed.

As Gianna released her, Annie looked up at Seth. “How was it,” he asked.  
Annie hugged Seth, kissing him on the cheek. “I loved it, Daddy. Thank you.” Gianna was standing next to them. Annie kissed Gianna on the cheek as well. “Wanna go again once daddy’s good?”  
Gianna grinned. “I’d love to.”


	13. Moving Lines, Part II

**Summary for the Chapter:**

> Jason finds himself in an awkward situation.

**Notes for the Chapter:**

> Moving Lines, parts I and II run concurrently.

Diana and Jason watched as Seth and Annie pulled off. Jason looked at Diana. “He’s still pissed at me.”  
Diana looked at him. “Yes. But don’t worry about it. He’ll be alright,” she said with a knowing smile.  
“What do you mean by that,” he asked.  
Diana shook her head. “Nothing. Let’s go back to the hotel. I just hope they don’t get pulled over.”  
Jason got in the Jeep and looked at Diana. “I can drive, Miss. I only had the one.”  
Diana put her hand over his mouth. “One drink is one too many when it comes to driving.”  
Jason was about to protest when he remembered about Angela, and nodded obediently.  
Diana kissed him on the cheek. “Good, puppy. I hope you’re ready for the surprise I’ve got in store for you,” she said as she rubbed his balls. He groaned slightly at the touch. “Your sore balls,” she said. 

Jason found himsef frog tied in front of the bed, naked and locked. He wasn’t gagged, which was a slight relief. He took a moment to examine his bonds: white cotton rope secured his wrists to his bound thighs and ankles. Diana also bound his arms to his torso, and ran a rope around the back of his neck and under the ropes securing his arms. “Get comfy down there, Princess. We’re gonna have some fun,” she said.  
Jason thought about it for a moment, and he actually was comfy.  
There was a knock at the door. “Don’t move,” she said with a giggle.  
Jason smirked as Diana left. A moment later, she returned with Tristan in tow. Jason’s heart raced in anticipation and slight fear. “Tristan, my puppy and I are going to take good care of you tonight, if you’re interested.”  
Tristan looked over the situation as Diana slid out of her robe. Before Tristan could say anything, she was kneeling in front of him, stroking his cock.  
Tristan looked down at Diana. “Oh, I’m interested,” he said with a glance at Jason.  
Dianna stood up and led Tristan over to Jason by his erect member. She knelt beside Jason and looked him in the eye. “You know you want to,” she taunted.  
Jason hesitated, but was relieved when Diana made the first move. She expertly took Tristan into her mouth and bobbed her head back and forth.  
She slid him out and looked at Jason. Jason looked at her, then Tristan. He leaned forward and licked his tip. He realized he was clean and slowly took the other man into his mouth. He felt dirty, but not wrong.  
Jason let himself get into the action. He bobbed back and forth on the tall, slender man. As Jason was getting into it, he watched as Diana pushed him back. “Don’t bogart that cock,” she said.  
Jason licked his way down to the man’s balls. His sack was freshly shorn, which made him happier. It was weird enough he was pleasuring another man, let alone if he’d have to fight pubes. 

Jason was startled as Diana grabbed him by the top of his head and pulled him away from Tristan. “Just kneel there for a moment,” she said.  
Diana laid down on the bed as Tristan kissed his way down her body. Jason felt his cage start to get tight, wishing that was him. Diana looked over at him and made eye contact as Tristan made his way to her wetness. She gasped loudly while looking at Jason. Jason’s cage started throbbing. “Princess, make yourself useful and eat his ass!”  
Jason hopped over to behind Tristan. He hesitated for a moment, but Tristan wasn’t having any part of it. He pulled Jason’s head between his legs, a way to show him who’s in charge.  
Jason closed his eyes and imagined he was servicing Diana. He licked and kissed at the puckered orifice. He heard moaning coming from two people. Knowing he was pleasing two people made this all worth it.

Jason started getting into the part just as he felt himself being hefted onto the bed. Diana and Tristan were both lifting his bound body. Jason locked eyes with Diana as they laid him down. She winked at Jason and blew him a kiss.  
She stopped at his ear. “You’re doing fine,” she whispered as she straddled his head.  
She laid down in a 69 position, and pulled his head into her pussy and ass.  
“Eat me,” she commanded.  
Without hesitation, Jason devoured Diana’s holes. He moaned loudly as she serviced Tristan at the same time. Diana didn’t take long to cum. And when she did, she soaked Jason’s face, nearly drowning him in her fluids.  
He slapped his leg twice. Diana saw this and stopped everything. She dismounted her submissive and looked at him. He was gasping for air while slowly stroking Tristan.  
“Speak, princess,” she said.  
Jason was breathing heavily. “I just needed to catch my breath.”  
Diana kept stroking Tristan as she slid a finger in Jason’s ass. “No rush, but this is hot,” she exclaimed.  
Jason looked at her. “Green.”

Diana kissed him on the cheek as she straddled his face again. Jason continued to lap at her wetness as Tristan slid his manhood into Diana. She gasped as he penetrated her. Jason went back and forth between licking Diana’s clit and Tristan’s rod as he thrust into her.  
Tristan stopped thrusting into Diana and slid into Jason’s mouth. Jason was caught by surprise, but went with it. No sooner than Jason got used to Tristan in his mouth, he slid back into Diana. 

Before Jason knew it, Diana was fumbling with his cage. Jason suddenly had a sense of freedom as Tristan moved away from her wetness. Diana was up by Jason’s ear. “I’m going to let you cum, Princess. But Tristan is going to be in your ass when you do.”  
Jason was desperate. He didn’t care. He was nodding like an idiot and didn’t notice Tristan had lubing his ass. Jason looked down to see Diana slow stroking him. Jason gasped as Tristan entered him. As Tristan thrust, Diana stroked. As Diana stroked, Jason moaned.  
Diana kissed him hard as she stroked him. She could tell he was getting close. She broke the kiss and started sucking Jason off. “I’m gonna cum,” he yelled as he exploded in her mouth.  
Jason relaxed from his orgasm, but Tristan was still fucking him. Diana came up for what he thought was a kiss, but she pushed his load into his mouth. Jason dutifully swallowed every drop.

Diana climbed off of Jason as Tristan slid out of him. They helped Jason off of his back and into a kneeling position beside the bed. Tristan slid off the condom he was wearing and jerked his cock in front of both of them. Jason leaned forward and started to suck Tristan off while Diana stroked him.  
“I’m cumming,” Tristan groaned.  
Jason instinctively tried to slide off of Tristan, but Diana held his head in place as Tristan exploded in his mouth. Jason choked on his hot load as he swallowed it whole.

Diana released Jason’s head and kissed him. She’d never kissed him like this before. Tristan let them be for a moment as he went to use the restroom. Diana slow stroked Jason’s manhood. He started to get hard in her hand.  
“How do you feel, puppy?”  
Jason looked at her. “Dirty. I need to know, Miss.”  
Diana looked at him, wrapping an arm around his neck to bring him in closer. “Ask away.”  
Jason looked at her. “Did you enjoy having me please Tristan?”  
Diana leaned back, showing him her dripping wet pussy as she fingered herself. “Look at me. Do you see how wet I am?”  
Jason looked down at her. “Yes, Miss.”  
Diana smiled. “I am VERY pleased. I also want you to know that I don’t think you’re gay for any of this. I wanted you to get fucked by another man, and being part of it made me happy. You’ve moved a line today, Princess. I want you to know that.”  
Jason smiled. “Thank you, Miss.”  
Diana reached behind Jason and began untying his bonds. “I want you to get up, move around, and get the blood flowing again.”  
Jason smiled. “Yes, Miss.” He looked down to see his legs freed. Diana helped him up as Tristan came out of the bathroom.

Tristan looked at them as he pulled his clothes back on. “I can’t stay for another go. I have the early shift tomorrow.” He kissed Jason on the cheek. “You were good.”  
Jason squeezed Diana. “Thank you. You were my first,” he said as he watched him kiss Diana.  
Diana walked Tristan to the door and let him out. She locked the dead bolt behind her. “Now, what was I about to do? Oh yes! Once you’ve recovered, I’m going to make you feel like a man again!”


	14. A turning point

**Summary for the Chapter:**

> Jason and Diana share an experience that change their relationship forever.

Diana woke up and looked at the alarm clock. It was 7:45am. She looked down to see Jason holding onto her. She smiled as she remembered their night last night. She could still smell the testosterone that had built up in the room.  
She gently unwrapped Jason from her waist and went to use the bathroom. When she finished her business, she happened to see a note come through the crack in the bottom on the door. She picked it up and read the note.  
She turned around to see Jason sitting on the toilet. “Good morning, Princess.”  
He looked up at her, still half asleep. “Good morning, Miss. Did you sleep well?”  
She smiled and nodded. “I did. I hope you did, too. We’ve been summoned to Mistress Eva’s room. We’re expected to be there at 9:00. I suggest you take a fast shower. I won’t have time to edge you, I’m afraid.”  
Jason stood up and flushed the toilet. “I understand, Miss.” He reached in and turned the shower on.

At 8:57, Diana knocked on Eva’s door. Jason was in tow, donning his homemade leash and rope collar. The busty brunette answered her door, wearing a silk bathrobe. “You’re early. Come in,” she commanded.  
Diana and Jason stepped into her suite, closing the door behind them. Jason began stripping naked, as was his usual custom whenever entering a Dominant’s room.  
Eva thought nothing of it and looked right at Diana. “You have a well behaved submissive,” she praised.  
Diana felt a red flag raise immediately. “Thank you, Mistress Eva.”  
Eva looked at her. “However, he seems to be lacking in his training. Tie him to the chair,” she instructed as she pointed to the corner.  
Diana took him by his lead and led him to his seat. As she bound his wrists behind his back, she leaned into his ear. “I don’t like this,” she hissed.  
“Neither do I,” Jason hissed back.  
Diana finished tying him to the chair, his ankles bound to corresponding chair legs.  
Eva pointed to the bone gag Jason was wearing around his neck. “Gag him, tightly,” she commanded.  
Diana looked at Jason and did as she instructed. 

Jason watched helplessly as Eva led Diana to the footrest of the bed and handcuffed Diana. She pulled against her bonds as Eva stuffed what looked like a G string into her mouth and wrapped duct tape around her head.  
Jason pulled against his bonds and grunted into his gag loudly. Diana also offered muffled protests.  
Eva cracked a flogger against Diana’s chest. “Silence!” Both Diana and Jason got quiet and Eva continued. “Since you seem to have trouble controlling yourself, I’m going to have to take matters into my own hands.”  
Diana pulled against her handcuffs as Eva started to suck Jason off. Jason pulled at his ropes as he wasn’t sure what was going on. Eva bobbed her head up and down, tasting precum on Jason’s member. Jason couldn’t help but enjoy what he was feeling.  
Before he knew it, Eva stopped sucking him, and stroked him fast. She wrapped her lips around the tip as he exploded in her mouth. She sucked his load from him like a golf ball through a garden hose.  
But she didn’t stop stroking him. In fact, she focused on the tip of his cock. He started laughing and pulling against his bonds as she rubbed him, using his cum as a lubricant. Diana yelled at her through her gag, but Eva didn’t stop.  
“Are you going to make another mess downstairs,” Eva yelled at him.  
Jason screamed “No, mistress” through his gag.  
Eva didn’t stop. “I don’t believe you!”  
Jason screamed again and pulled violently at his bonds. 

Before Jason knew it, Eva fell limp, letting go of him. He relaxed and looked up at Diana, who had one of her wrists free, and was holding a lamp.  
She pulled the tape off of her head and removed Jason’s gag. “Are you alright?”  
Jason kept catching his breath as Diana untied his ropes. Since she tied the knots, she had no trouble untying him.  
Once he was free, they hugged each other, both an emotional mess. “She’s no mistress,” Diana said.  
Jason held her. “I could tell, Miss.”  
Diana kissed Jason, their tongues exploring each other’s mouths. Jason broke the kiss and looked at her. “I feel safe with you, Miss.”  
Diana smiled and looked at Jason. “Get dressed and go back to the room,” she said.  
“Yes, Miss,” he replied.  
Once he was gone, Diana looked at Eva, the wheels turning. 

Diana returned to their room to see Jason packing the bags. “You read my mind,” she said.  
Jason looked at her. “If I never go to another con again, I’ll be happy.”  
Diana took ahold of his hand and looked at him. “Kneel, and listen, puppy.” Jason obeyed instinctively as Diana sat down in front of him. She held the sides of his head and looked at him. “What she did to you...to US, was wrong. If I had known what awaited us when I read that note, I never would’ve went to her room.”  
“What do we do now? Can we file charges against her,” Jason asked.  
Diana shook her head. “It wouldn’t do any good. The case would never make it to trial. Her lawyers would want drag us through so much legal red tape it wouldn’t be worth it.” Jason was as frustrated now as he was an hour ago. “But, we could blackmail her,” she said as she showed Jason a picture of her on her phone.  
Jason looked at the picture of Eva Notty, duct taped to the very same chair he’d just been tied to, gagged with layers of duct tape. “Will you let me touch myself to this, Miss?”  
Diana smirked. “Ok, Princess. Just this one time, and under my instruction.”

Diana wiped Jason’s load from his stomach and fed it to him. Jason expertly cleaned her fingers off before he was locked again. “Finish packing, Princess. I’ll be back shortly.”  
Diana left their room and went down the hallway. She knocked on the door and Annie answered. “Miss Diana. Please come in.”  
She entered the room. “Thank you. Is Seth here?”  
Almost in response, Seth came around the corner, pulling his pants up. “What's going on?”  
“Jason and I are leaving today,” Diana said as she showed Seth the picture she’d taken of their hostess.  
Seth adjusted himself. “What happened?”  
Diana looked at him. “Remember how he ruined Annie’s blouse?” Seth nodded. “Well, Eva decided to punish him without either of our consent.”  
Annie took ahold of Seth’s arm and looked at him. “I don’t like this,” she said.  
Seth held her. “I know. Is he ok?”  
Diana shook her head. “Not right now, but he will be.”  
Seth looked at her. “Is there anything we can do?”  
Diana looked at him. “He’s traumatized enough over this. And he’s convinced you hate him.”  
Seth looked at her. “Say no more. I’ll talk to him,” he said.

Diana returned to her suite with Seth and Annie in tow. Jason looked up as Annie came in and hugged him. Jason felt his cage start to get tight and tried to think unsexy thoughts.  
“I’m sorry,” Annie said, almost in tears.  
Jason hugged her. “It’s ok. I’ll be alright.”  
Seth walked up to him, Annie still holding onto him. “Hey. You and I, we’re ok,” he said as he offered him his hand.  
Jason took it. “Thank you.”  
Annie looked at him. “I also want you to know that we’re leaving the con, too. For the hostess to do this to one of her guests is uncalled for.”  
Jason shook his head. “I don’t want you to pack out because of us.”  
Seth looked at him. “For us to stay after this would be agreeing with her actions. Diana and I are thinking about addressing the con.”  
Jason looked at them. “I’m coming with you,” he said.  
Diana looked at him. “No, Princess. I want you to finish packing our bags, then help Annie with theirs.”  
“Yes, Miss,” he answered.  
Diana, Seth, and Annie left the room as Jason finished packing their bags.

Jason knocked on Annie’s door. She opened obediently. “Do you need any help,” he asked her.  
Annie let him in and closed the door behind her. “Sit down for a minute,” she said.  
Jason sat down and looked at Annie. Before he could say anything, she kissed him. Her tongue exploring his mouth. Jason embraced the woman for a moment, then pushed her away slightly. “I’m sorry. I can’t do this,” he said.  
Annie held his hand. “Jason, talk to me. Please?”  
Jason stood up and sat her down on the bed. He locked eyes with her. “After Eva tied me to the chair, I wasn’t sure what was happening. Before I knew it, she took out my safety net.” He felt himself choke up slightly. “For the first time since I met Miss Diana, I felt afraid. Not afraid of what was going to happen, but afraid I’d get hurt.”  
He walked away from her and looked out the window. “There’s nothing else to say. Except it was fun while it lasted.” Annie hugged him from behind. Jason cowered at her touch and turned to face her. “I’m sorry. I won’t forget you,” he said with a kiss to her cheek.  
Annie looked at him. “Jason, talk to me. Please.”  
Jason shook his head. “There’s nothing to say. Let me help you with your bags.”

About an hour after Seth and Diana left, Jason was pulling two luggage trolleys out of the elevator into the lobby. Seth and Diana had already checked out of their rooms and pulled their cars around to the front of the hotel.   
Seth looked at Jason. “The trunk is full. Would you mind putting the bags beside our car, please?” Jason nodded as Annie gave Seth an odd look.   
Diana looked at Annie, then again at Seth. “If you guys ever need anything, don’t hesitate to call or text.” She kissed him on the cheek and shook Annie’s hand. “You’re a good girl,” she said.  
Annie bowed. “Thank you, Miss Diana. Take care of Jason. He doesn’t seem the same to me. Almost disconnected.”  
Diana looked at her. “Disconnected how?”  
Annie shrugged. “I’m not sure. I just know he doesn’t have the same fire he had when we first met. I think Eva fucked him up.”  
Diana pat her on the shoulder and walked out to the Jeep. “Be kind and say goodbye to our friends, Princess.”  
“Yes, Miss,” came his response. Jason walked over to Seth and cast his eyes down. “Good bye, sir.”  
Seth and Jason shook hands. “Good bye, Jason. I hope everything works out for you.”  
Jason shook hands with Annie. “Good bye, Annie.”  
Annie pulled him in for a hug. “Don’t keep this to yourself,” she whispered into his ear as she let go of him.   
Jason made sure Diana was safely in the Jeep before getting behind the wheel himself and heading back to Michigan.


	15. A Dark Corner

**Summary for the Chapter:**

> Jason deals with the repercussions of the con.

**Notes for the Chapter:**

> This chapter takes place two weeks after the couples left the con.

Diana paced nervously. Jason has kept himself holed up in the basement since they got home from the convention. He would come up only to go to the bathroom and shower. She would edge him while he was in the shower, but he hasn’t been the same. He seemed detached somehow.

She knelt down by the door to the basement and put her hand up on it. “Princess?”  
Silence. She tried again. “Princess!”  
Again, silence. She stood up and opened the door slowly. As she made her way down the stairs, she feared the worst. Luckily, she overthought it. Jason was laying on the floor, naked, fast asleep. She looked him over. His hair was unkempt, he hadn’t shaven anywhere since they got home. He looked like hell! Diana curled up behind him, careful not to wake him, wrapped her arms around him, and zoned out. 

When Diana woke up, she realized she was being held. Jason had turned and wrapped his arms around her. She leaned up to him and kissed his hairy chin. “Princess?”  
Jason shifted and looked at her. He realized what he was doing and released her. He knelt before her, keeping his eyes to the floor. “I’m sorry, Miss. I didn’t mean to touch you like that without permission.”  
Diana pat him on the head. That was the most he’d said to her, let alone anybody, since they’d come home from the con. “It’s ok Princess. I’ve been worried about you.”  
Jason kept looking at the floor. “Don’t worry about me. I’m fine.”  
Diana stood up and lifted his head by his chin, forcing him to look at her. “No, you’re not. You’ve given everyone the silent treatment since we left Chicago. I know she made you feel unsafe. But, she’s been dealt with.” She looked away to wipe her eyes and regain her composure. “I miss you, Jason,” she said crying.  
Jason looked at her, standing up and hugging her. “I’m sorry,” he said as he fought back his emotions.  
They kissed in unbridaled passion. Not as Domme/sub, but as man and woman. Their hands explored each other’s bodies. Diana looked into his eyes and took ahold of his chaste member. “We both need this,” she said. “Please come upstairs, to my bed.”  
Jason agreed.

Jason watched as she knelt before him and unlocked his cage. His cock sprung to life, obviously a result of two weeks of edging. She stroked him slowly as she looked into his eyes. “Do you trust me?”  
Jason nodded. “Always, Miss.”  
Diana stood up and laid him down on the bed. She kissed him again, straddling him and rubbing herself against his throbbing manhood. She took care not to set him off early. As they kissed, she felt her panties getting soaked. She stopped rubbing against Jason and sat up. She took his hands and pushed them against his chest. “I want you to enjoy me, Jason.”  
She straddled his face, pushing her panties to the side, and lowered herself onto him. She moaned and giggled as his hairy mouth lapped at her wetness. She kinda liked the idea of him with a beard. She ground on his face while reaching out and stroking his manhood.  
It was a blowjob turned unwanted post orgasm torture that sent him into this dark corner. Diana figured the best way to bring him back was to show him he could trust her in that regard. She stopped stroking him and moaned louder. She quivered as she sprayed his face with her juices.  
She turned around and kissed him, tasting her juices on his tongue. She felt him wrapping his arms around her. She pushed him off. “Not yet. I’m not finished with you.”

She kissed her way down his body to his pulsating member. She took him into her mouth expertly. She bobbed up and down on him, and listened as Jason moaned in pleasure. Hearing him enjoy her was making her wet again. She was tempted to ride him, but that wasn’t her purpose.  
“Cum in my mouth,” she said as she stroked him fast. She locked her lips onto the head as he stretched out his legs. She swirled her tongue around him once, setting him off. He groaned loudly as she took his load into her mouth. She felt him stop shooting, gave him a slight suck of the head to catch it all, and showed it to him.  
She crawled up to his face and locked eyes with him. As she showed him his load, he opened his mouth obediently. She put a hand over his mouth before swallowing.  
He looked at her, watching as she laid down next to him. “We both know, in more ways than one, you needed that. I don’t want to lose you,” she said as she kissed him.  
He kissed her back and the two laid in bed for a while. Diana got up. “Go take a shower, Princess. Do not wash your face. I want to take you out for dinner tonight. I’ll pick out a change of clothes for you.”  
“Yes, Miss,” he said as he got up and went to the bathroom.

Diana stepped into the bathroom in time to see Jason about to wash his crotch. “Don’t touch it,” she said with a smile.  
Jason smiled and washed around his genitals. Diana watched and felt her thighs start to sting a little. “I like the way that beard looks on you, Princess. But, my thighs hate it. You’re gonna have to shave that shit off,” she said.  
“Yes, Miss,” was all he said as he offered her the loofa. She stepped into the shower and played with him slowly. Once she felt him get hard, she decided to wash him thoroughly. “This needs a shave...or wax, too.”  
“A wax,” he asked her.  
She nodded. “Especially if I decide to collar you. A shave won’t do for that,” she said as she looked up and winked at him. “Rinse my cock off,” she instructed.  
Jason took down the shower head and ran some water over his crotch. Once he was rinsed well, Diana kissed the head before teasing it again. She edged him until she felt the water start to get cold. “Shut off the water,” she said. She stepped out and came back in with a can of shaving gel. She lathered his crotch and shaved him down, being careful not to nick him with the razor.  
After ten minutes, which consisted of a shave and one more edge, she licked the precum from his head. “Rinse off and get out.”

Jason stroked his chin, which was smooth for the first time in two weeks. He flipped down his visor and adjusted his bow tie as Diana pulled up in front of the Olde Penninsula. He’d never been here before, but Diana knew what he liked. He smiled as she rubbed his arm.  
As Diana shut off the car, they looked at each other. “I know how you like to get dolled up every now and then,” she said as she played with the small key that laid against her cleavage just right. Jason was glad she picked out a pair of dark pants for him to wear. Jason adjusted his shirt collar slightly.  
“You know me too well, Miss.” He looked out the window before getting out. He walked around to her and held the door for her. As they walked into the pub, she slid her hand into his back pocket. They slid into a “quiet” booth in the corner and sat next to each other. She dropped a napkin into his lap, but not before she unzipped Jason’s fly and squeezed his balls. He shifted uncomfortably as she smiled. “Control yourself,” she instructed.  
Jason held up the menu as they both looked through it. They both had the Olde Smokey with the house root beer. While they waited, Diana teased Jason’s caged cock. She looked at him, an evil smile forming on her face. “If you don’t stop leaking, I’m going to make you cum like a bitch,” she hissed into his ear.  
Jason smiled at the idea. “What if I refuse?”  
Diana gave him a squeeze, causing him to grab the bench with both hands. She chuckled. “I don’t think you will. I promise to be gentle.”  
Jason relaxed as she loosened her grip. “I still trust you, and feel safe with you, Miss.” Jason leaned his head on her shoulder, and Diana held him until their food came. 

Diana tossed Jason the keys. “Take the long way home.”  
Jason got Diana loaded into the car before he took his place behind the wheel. He started the engine and pulled out of the lot. Diana opened his fly and pulled out his caged cock. He looked down at her, then suddenly back at the road. Before he knew it, he heard the unmistakable sound of a lock being clicked unlocked. He suddenly felt his cock get hard.  
Diana kissed his purpling ball sack as she slowly stroked him. “Eyes on the road and hands on the wheel,” she instructed. She took him into her mouth expertly. She could taste his approval as his cock leaked precum at the slightest touch. Jason shifted slightly in his seat, and Diana allowed it.  
Jason thanked god silently that the windows were tinted dark. He felt Diana very gently and slowly bobbing up and down on his throbbing member. “I’m getting close,” he told her.  
She stopped and looked at him. “Control your breathing.”  
Jason got himself under control, as Diana resumed her slow stroking and sucking. He felt himself enjoying it more and more. “I’m getting close again,” he said. She didn’t stop. His breathing got heavier. “May I please cum?”  
Diana stopped and squeezed his heavy balls. “No, Princess. Control yourself. If you behave, I’ll let you cum when we get home.”  
Jason slowed his breathing and regained his focus. Diana resumed her tortuous blowjob. It didn’t take long before Jason felt himself building up again. “I’m close again!” He rested his hand on her neck, which caused her to let go with her hand and lips.  
She looked up at him. “If you touch my neck again while I’m doing this, I’ll ruin it and you’ll sleep on the floor next to my bed.”  
Jason shifted in his seat. “I’m sorry, Miss.”  
Diana looked at him. “Good boy.” She looked out the window, knowing he was minutes from the house. “I’ll bet I could make you get close two more times before you get to the house,” she said as she licked her thumb slow stroked the sweet spot of his cock.  
Jason’s breathing hitched and he groaned loudly. “May I please cum, Miss?”  
She let go of him. “Nope.”  
Jason whimpered, then realized Diana was glaring at him with a half grin. “I don’t know where that came from.”  
“I do,” she said as she held his cock by it’s base and slurped on the head again.  
Jason moaned and hitched as she brought him close again. “God please may I cum, Miss?” Jason felt himself almost to the point of no return.  
Diana looked up at him as she kept slow stroking him. “No. Hold it!”  
Jason groaned loudly, holding on to the orgasm for dear life. “I can’t take it anymore,” he said behind grit teeth.  
Diana let go of him and watched as his cock twitched with need. She smiled as his member took on a shade of crimson she’d only seen once before.  
Jason backed the car into the driveway. As he shut off the engine, Diana pulled him over to her and kissed him, driving her tongue into his mouth. “Touch me,” she said.  
Jason ran his hands up her blouse, squeezing her breasts. She moaned quietly as she ran her fingers through his hair.  
She pulled him away from her gently. “Sit still,” she commanded as she forced his cock back into it’s prison.

Diana held Jason’s hands and looked him in the eye. “Princess, I want to pin you to the bed.” She held up a pair of hand cuffs in one hand and held is hand with the other. “I’d cuff them in front of you, and I won’t gag you. I don’t want to do too much to you.”  
Jason examined the situation and looked at her. “I trust you won’t intentionally hurt me, Miss.”  
Diana kissed his cheek. “That’s my good puppy,” she said as she slapped one cuff closed around his wrist. She slid his wrists between two of the slats of the foot board and cuffed his other wrist. She watched him for a moment, then looked him in the eye. “If something doesn’t feel right, I expect you to tell me right away.”  
Jason nodded. “I’m ok, Miss.”  
Diana kissed him before she examined her pet, who was bent over the foot board of the bed. He was naked, caged, and was still wearing the plug she’d slid inside of him before they went to dinner.   
Diana caressed his back with her finger tips. Jason quivered at her touch. She knelt down behind him, looking at his plug. She kissed his cheeks lovingly. “I’m going to take good care of you.”  
She walked over to the night stand. “Watch me,” she instructed. As he looked up, she opened the drawer and took out her strapless strap on. He watched as she lubed it up, sliding the curved portion inside her pussy. As she walked back over to him, she felt the strap on rubbing her last bits just right.   
Jason looked at her. “I thought you said you’d let me cum when we got home.”  
Diana slapped his ass, then made him look at her. “I did. I never said how, Princess.”  
She knelt again and unlocked Jason’s cage. As she removed his metal prison, he immediately rose to greet her. “Well hello,” she said as she kissed him on the head. She gave a gentle swirl of her tongue, which caused Jason to moan and leak. “That’s my puppy. Are you ready,” she asked as she slowly stroked his erect member.   
“Yes, Miss. God I need this,” he said.   
“How badly, puppy?”  
He cranes his neck to look back at her. “Badly.”  
She smiled and slowly spreads his cheeks open. “Relax,” she says. She slowly pulled the plug out of him and grinned as his hole stayed open. She leaned forward and flicked him with her tongue. He instantly pushed back into her gently. She held up a hand and pushed him away. “Easy, Princess.” She looked down to see his cock pulsating, and a strand of precum leaking. She wiped the strand from him and fed it to him.   
“God I good,” he said. She leaned in and kissed him. He was lost in her kiss. “Take me, Miss. Please!”  
She let go and moved behind him. She sat a bowl down under him to catch his load before stroking him, which was rewarded with a quiet moan. She slowly rubbed the tip of her dildo against his hole, and he tried to back into it. She backed up. “Easy, puppy.”  
She tried again, this time she slipped the tip inside of him. He instinctively backed into her, but stopped himself before he backed up too far.   
“Good boy,” she said as she thrust into him. He moaned as she had her way with him. She continued to stroke him as she thrust. He moaned, biting his lip to keep from getting too loud.   
“Oh, god,” he exclaimed.   
Diana tugged at his manhood, timing it with her thrusts. “Don’t cum until I tell you,” she said. She could tell he was getting close.   
His moans got louder and he started backing into her. Diana was getting wetter and wetter. She stopped thrusting and squeezed his balls. He groaned in pain.  
“Get control of yourself,” she said. “I think you’re liking this too much.” He slowed his breathing and relaxed. She thrust into him and stroked him again. “That’s my good boy.”  
Jason ground against her as she toyed with him. He moaned again, as she got back into her groove. “I’m not stopping this time,” she said. She kept thrusting and he moaned louder.  
“Oh god, I’m getting close! Can I cum?”  
Diana smiled. “No. Hold it in!”  
Jason groaned and bit his lip. He held it in as long as he could. He didn’t want to disappoint his Miss. She leaned up and nipped his ear. “Cum for me, puppy.”  
Jason let go of his lip, and his control with a loud moan. He felt his balls lighten as she pulled out of him.

Diana slid the strap on out of her and sat down in the bed in front of his nose. “Eat,” she commanded.   
Jason eagerly burried his face between her legs again. She ground against his tongue, moaning louder and louder before finally exploding on him in a wave of pleasure and fluids.   
She pushed his face away from her as she stood up. She returned with the bowl and held it up to her. “Drink it,” she said.  
He eagerly lapped the bowl clean as Diana locked his cock back up. She unlocked the hand cuffs and pulled him up to her. Jason reared his head in her lap, wiping away a single tear that fell from his eye. He was starting to cope with things. “May I sleep in your bed tonight, Miss?”  
Diana looked at him. “I thought you’d never ask.”


	16. Relocating, Part I

**Summary for the Chapter:**

> Seth’s recent activities bite him, and change dynamics across the board.

**Notes for the Chapter:**

> This chapter contains some time jumps.

THREE WEEKS AGO

Diana backed Seth’s car up to a rear exit of the hotel. Seth was standing at the door having a cigarette with his foot resting on a duffle bag. Diana put the car in park and popped Seth’s trunk. Before Diana could get out and help him, he’d rolled the duffle into the trunk.

Diana put a hand on his arm. “It’s not too late, you know.”  
Seth looked at her. “I’m all in at this point. And if anything goes down over this, I’ll take the fall. I do, however, have a request.  
Diana looked at him. “Name it.”  
“If this turns to shit, please take care of Annie,” Seth requested.  
“I will. Any restrictions I need to know about,” Diana asked.  
Seth shook his head. “As you see fit.”  
Diana nodded. “You got it. But how will I know if I’m needed?”  
Seth looked at her. “Annie will call you.”  
Diana nodded and looked in the trunk at the duffle bag. “Don’t get stupid on the way home.”  
Seth opened the bag and revealed Eva Notty’s head. Her eyes were closed, and she had a ball gag in her mouth. “I won’t,” he replied.

NOW 

Diana awoke to her phone ringing. She looked to see it was Seth calling. “Hello,” she said groggily.  
“Miss Diana,” came a scared voice. “Seth told me to call you if something went down.”  
Diana stepped out of the room. “Tell me what happened, from the beginning.”

LAST NIGHT

A knock was heard at the door. Annie yelled down into the basement. “Daddy, there are cops here!”  
Seth wrapped tape around Eva’s mouth before coming upstairs, muffling her protests before she could say anything. He looked at Annie. “If they take me, you’re to call Diana. She knows what to do.” Annie looked at him and nodded as Seth went to the door. “Who is it,” he asked.  
“Detective Adams. I wanna talk to you.”  
“How many of you are there,” Seth asked.  
“Two; myself and Officer Williams,” he responded.  
Seth looked at Annie and smiled. “Then talk to each other!”  
Annie smirked as an envelope slid under the door. “That’s a warrant to search your residence,” Adams said. “We’re looking for some meth.”  
Seth cleared his throat before unlocking the door. “Come on in gents. Why go through the trouble to get a warrant? We’re clean here.”  
Adams stayed with Seth as Williams began looking through the home. “We received an anonymous tip from a reliable source, and we just want to follow up.”  
Seth watched as Williams went upstairs. “You can be assured...”  
Adams held up his hand. “Do you hear something?”  
Seth listened as he heard Eva trying to tell for help. Adams called for Williams to come back downstairs before making his way downstairs. A few minutes later, Adams brought Eva back upstairs wrapped in a blanket. “This is Eva Notty. She was reported missing from a convention in Chicago a few weeks back.” Adams looked at Seth. “Place your hands behind your back. I’m taking you downtown for questioning. You have the right to remain silent...”

“I’ll be there as soon as I can,” she said as she hung up. Diana looked at the time on her phone. It was 1:15am. She decided a late night edging session with Jason was in order. She pulled the covers off of Jason and rolled him into his back. “Wake up, Princess.”

Diana woke up at 6:45. Jason was shaking in pent up frustration. He hadn’t slept all night. Diana kissed the back of his neck, causing Jason to groan. “Good morning, puppy. I hope you got some rest. I have some business to attend to in Missouri. I’ll be away for a few days. Do not sleep in my bed while I’m gone. You may, however, sleep with my pillow.”  
Jason knelt before her and kissed her feet. “Yes, Miss. Do you have any other instructions for me?”  
Diana stood him up. “Keep this place running and clean. I’ll call you when I get there.”  
Jason bowed respectfully and packed her a bag to last her about five days, just in case she needed some extra time. 

SIX HOURS LATER 

“I’ll email you a list of extra things I want you to do for me while I’m gone. We’ll do them on FaceTime. Be good, Princess.” Diana hung up the phone. She was surprised to see Annie waiting for her. Annie ran up to her and gave her a hug. “Miss Diana,” she said, her voice cracking.  
“It’s ok,” she said. “I’m here now. I’ve got a hotel room I need to check into.”  
Annie shook her head. “Please...I don’t want to be alone again. Stay with me, ok?”  
Diana would normally be upset she was being bossed around like this, but she kept in mind that Annie’s world was just turned upside down. “Ok, Annie. I’ll stay with you.”

Diana sat down in the visitor’s area where Seth was being held. A guard brought him in. Seth looked no worse for wear; his hair was unkempt, he hadn’t shaven, but otherwise no worse for wear. “How are you holding up,” she asked.  
Seth looked at her. “I’m doing ok. One of my safety briefs I got at work once was ‘Don’t add to the population, don’t take away from the population, and if I ever go to prison establish dominance quickly’. So far, so good. We don’t have any money for bail, so I’m stuck here until my court date.”  
Diana looked at him. “What do you need from me?”  
Seth leaned in. “My brother is going to be moving into the house in a couple of days. Everything of value has been moved out and stored. I need you to take care of Annie for me. Care for her as you see fit, with one exception: she is not to have the touch of another man. Do you understand?”  
Diana nodded. “I do. I’ll keep an eye on her. But, I’ll have to take her back to Michigan with me.” Diana slid him a sheet of paper. “Here’s my address, phone number, and if you have the ability my email.”  
Seth took it and held it up for the guard to look at. After a moment, the guard returned it to him. “I know she’ll be in good hands with you,” he reassured her. 

LATER THAT EVENING 

Jason answered the FaceTime call. He was wearing a pair of gym shorts, and his metal gilded cage. “Hello, Miss. To what do I owe the pleasure?”  
Diana looked at him. “You’d better be naked right now,” she commanded. Jason shuffled quickly before kneeling. “Show me,” she said. Jason aimed the camera down, showing off his purple cock and balls. “Good puppy,” she said. “Go into the night stand and set up the dildo. I wanna watch you,” she said.  
“Yes, Miss,” Jason said. He picked up the iPad and took it into the bedroom. He sat it down beside the footrest of the bed. She heard him open the night stand, then close it again. A moment later, she heard the satisfying SMACK of a suction cup.  
Jason picked the iPad back up and showed Diana. “Would it please you to watch me suck it,” he asked. Diana nodded as Jason knelt in front of the foot board and take the phallic toy into his mouth.  
Diana stopped him. “Now fuck it,” she said. Jason obediently sat the iPad down so the camera could pick up the action. Jason slid the dildo inside of him skillfully. He moaned quietly as the toy rubbed his P spot just right. Diana reached down her pajama bottoms and rubbed her clit. “That’s it. Don’t cum!” She fingered herself as she felt a wave of pleasure build up inside of her. “Don’t stop! I’m so fucking wet!” Jason moaned and bounced on the dildo faster. Diana moaned out, stuffing a clean pair of socks in her mouth to muffle her screams as she exploded in a burst of pleasure!  
Diana came down after a moment and realized Jason was still fucking the foot board. “Stop. Clean up your toy and go to bed,” she said.  
Jason stopped what he was doing. “Yes, Miss. Thank you, Miss,” he said.  
“Be good,” she said as she ended the call. 

Diana stepped out of the bathroom, having washed her hands. As she sat down on the couch, Annie brought her a glass of wine. Annie was naked, as were her instructions at the end of the night. Diana looked at her. “What’s this,” she asked.  
Annie looked at her. “Wine. Rosè to be precise.”  
Diana smiled. “Not that. Why are you naked?”  
Annie looked down. “It’s part of my night time routine to be naked for daddy. I usually bring him a beer, but all we have right now is the wine you brought.”  
Diana looked at her. “Get dressed and sit with me,” she said. Annie looked surprised, but did as she was told. She returned wearing only a silk bath robe. Diana poured Annie a glass of wine. The ladies sipped it together beside the fireplace. Diana looked at her. “Seth told me his brother is moving in for the time being.”  
Annie shifted slightly. “Yes, Miss.”  
Diana corrected her. “My name is Diana.”  
Annie nodded somewhat uneasily. “It May take me some time to get used to that,” she said.  
Diana smiled. “Which brings me to what I have to tell you next. Seth told me to take care of you, with the only provision that you do not have a man’s touch. I told him the only way I could do that would be to take you to Michigan with me.”  
Annie sat up. “I don’t want to be a burden, Diana.”  
Diana shook her head. “It’s no burden.”  
Annie took a gulp of her wine, realizing her life was about to change. “I don’t know what to say,” she said.  
Diana smiled. “It’s my pleasure.”  
Annie felt herself relax after she downed the last of her wine. She laid her head down on Diana’s shoulder. She relaxed a little more as Diana pat her head.  
“Oh, Annie. I can only imagine how tough this has been for you,” Diana said. “I’m just glad I could...”  
Annie cut her off with a kiss. She slipped her tongue in Diana’s mouth, lightly probing at her. Diana was caught off guard for a moment, but her dominant instincts kicked in and she gently pushed Annie off of her.  
Annie knelt before her. “I don’t know what came over me, Miss.”  
Diana stood her up. “I told you already. Call me Diana. However, you’re going to have to pay for this.” She took Annie by her arm and drug her into her bedroom. “Bend over the bed,” she ordered.  
As Diana looked for something to spark her with, she came across Annie’s strapless strap on. “Hello, what’s this?”  
Annie turned her head and smiled. “I was kinda hoping you’d find that, Miss.”  
“Really? And what were you hoping to do with this and me,” she asked.  
Annie swallowed. “I wanted to fuck you, Miss.”  
Diana giggled. “Oh, someone’s about to get fucked, alright.” Diana cleaned off the smaller end before sliding it inside of her. “How do I look. Nice?” Annie gulped. She was about to have her own weapon used against her. Diana pointed to the floor. “Kneel.” Annie slid to the floor and faced her dildo, “eye to eye” so to speak. “Suck it,” Diana told her.  
Annie took it in her mouth. She moaned as she imagined it was her daddy she was sucking off. “I need this,” she said.  
“I know,” Diana responded.  
Annie continued to go down on the phallic object, really getting into it. She felt Diana’s hand brace the back of her head, but didn’t try to force her onto it. Annie slicked her hand over the rubber toy. “Fuck me, Miss!”  
Diana stood her up and laid her on her back on the bed. As Diana mounted her submissive female, Annie opened her legs. Diana reached down and play with her clit. “God, you’re wet.” Diana touched herself. “So am I!”  
Annie giggled as she felt her pussy getting filled. Her giggles turned to moans as Diana thrust into her. Both ladies moaned as Diana gently thrust into her. “I could teach you so much,” she said.  
Annie responded by leaning up and biting Diana on her neck. Both women moaned again, louder this time. Annie let go. “Oh god, I’m gonna cum!”  
Diana kept her pace, feeling herself build up too. As if someone had snapped their fingers, both women screamed out as they exploded in eccasty. Diana laid down on top of Annie, and kissed her newest conquest. “Jason would be so jealous of you right now,” Diana said.  
Both women giggled as Diana slid out of her and put her new favorite toy on the night table. “Tomorrow you’ll pack a bag, and then we’ll go to Michigan,” Diana said.  
“Yes, Diana,” Annie replied. Diana pulled Annie closer, and they both trailed off to sleep.

Jason was waiting for the women at the airport. When he saw Annie and Diana come out of baggage claim, he bowed before them before loading their bags into the Jeep. “How was your trip, Miss?”  
As he held the doors open for both ladies, Diana looked at him. “Eventful,” she said. “Annie will be staying with us for a while,” Diana informed him.  
Jason looked back at Annie, feeling relieved. The car ride wasn’t long, but the silence was damning. After a 30 minute ride, Jason parked the car in the driveway. After he unloaded the bags, Annie and Diana were standing in the doorway. Jason walked up to Annie to give her a hug. She pushed him away. “Annie, it’s ok.”  
Annie gave him an unwavering look. Jason felt his knees turn to Jelly, and he heard the blood flow into his head when Annie spoke. It was only one word, but the word that she spoke resonated within him, all the way to his core.  
“Kneel.”


	17. Relocating, Part II

**Summary for the Chapter:**

> Dynamics continue to change between our friends

Jason froze. He couldn’t believe what he’d just heard. Before he could react, Diana reached out and squeezed his already sore and swollen balls. He cried out in pain as he fell to his knees. Diana let go of him, and he cast his eyes downward.  
Annie looked at him. “Things will be different around here for a while. I’d suggest you learn how to please the both of us,” she teased.

Annie slowly tied Jason’s wrists behind his back while Diana kept him in a kneeling position by having him eat her out. Diana moaned as she enjoyed her “welcome home” treat. “I could get used to this,” Diana moaned. As Diana enjoyed her princess, Annie bound his arms to his chest, effectively immobilizing them.  
Diana heaved and moaned loudly as she exploded on Jason’s face. She held his head in place as a riptide if fluids gushed from her satisfied pussy. She released him and took a step back. She smiled as she partook the view. “We’re gonna have so much fun, Princess.”  
Annie came around to stand beside Diana. Both women admired the bound and naked submissive with pure lust. Diana knelt in front of him, bringing him eye to eye with her. “What are your safe words, Princess?”  
Jason looked directly at her. “My safe words are ‘Green’, ‘Yellow’, and ‘Red’, Miss.”  
Diana didn’t blink. “What do they mean?”  
“‘Green’ means I’m good to go, or you can continue or start again. ‘Yellow’ means I need a moment, but I don’t want to stop what we’re doing. ‘Red’ means I can’t handle it and I need to stop, Miss.”  
Diana looked at Annie, then back at Jason. “What are your safe sounds should we gag you?”  
Jason didn’t flinch. “Thumbs up means ‘green’, knocking on something, or a clapping or slapping something means ‘yellow’“, he slapped his ass cheeks as a demonstration. “Snapping my fingers once is ‘red’.”  
Diana kissed him on the lips. “Good boy.” She stood up and looked at Annie. “I taste so delicious. Take a taste,” she said.  
Annie knelt down and kissed Jason on the lips. “Mmm, you really do taste yummy. Let me get some from the tap,” she said. Annie turned her head as Diana slipped her right leg over Annie’s shoulder. Annie lapped at Diana’s sweet wetness as Diana vocalized her pleasure. Jason knelt beside Annie, helpless to do anything but watch. He groaned as his cock swelled in its tiny metal prison. Diana has fit him with a smaller device when they all got home.  
Diana looked down at him, watching as his cock drooled a strand of precum, which nearly dribbled to the floor. “If you drip on my floor, you’re going to lick it up!”  
The act of Jason looking down was enough for his strand to touch the floor. He looked back up at her, as she pointed to the spot on the floor. “Clean it up,” she said with a moan.  
Jason backed up slightly and bent his body down to the floor. As he hovered, he felt Diana’s foot push his head into the floor. He turned his head to keep from popping his nose, smashing the puddle of precum against his cheek. “Naughty boy,” she said as she exploded on Annie.  
Annie looked at Jason. “This almost isn’t fair. I feel like we should do something.”  
Jason lifted his body with a grin. Before he knew it, he had a leather blindfold buckled over his eyes. His smile turned into an instant frown and whimper. Annie looked at him. “Much better,” she said. Jason could hear the unmistakable sounds of Annie moaning, leaving his imagination to run wild!

Annie and Diana were fast asleep in the bed, while Jason tossed and turned on the floor. His wrists were loosely tied behind his back to prevent loss of circulation and injury as he tossed.  
Diana heard him start to whimper in his sleep. She sat up and watched as he started thrashing in his sleep. She shook Annie awake and went down to the floor next to him. He jerked awake and looked right at Diana.  
“Are you alright, Princess,” she asked.  
He shook his head. “Are you ok? I dreamed that you two had left me here. And when Infollowed you outside, there was nobody. No one at all.”  
Diana took hold of his caged member gently and gave him a reassuring pat. “We’re here, and we’re not leaving you.”  
Annie sat down on the other side of Jason and hugged him from behind. “Not like that,” she reassured. Annie looked at Diana. “Let’s show him how much we love him.”  
Diana looked back at her. “What do you have in mind?”  
Annie grinned. “He’s been a good boy since we’ve gotten home. Let’s both enjoy him.”  
Diana kissed him full on the lips, her tongue exploring his hungry mouth. She got wet just feeling his tongue dancing around with hers. Annie took the opportunity to fit Jason with a strap on, his caged package poking out of the bottom of the harness. Diana broke the kiss and helped Annie bind his wrists in front of him, using a pair of handcuffs to secure his wrists to his caged package. Jason tugged, feeling an excruciating pull against his blue balls. Diana giggled at Jason’s situation as she looked at him. “You get to just lay here and enjoy what’s about to happen you you,” Diana taunted him.  
She presented a dildo gag to Jason, who eagerly opened and accepted it. Diana fastened the leather strap behind Jason’s head, effectively turning him into an animate fuck doll. 

Diana and Annie laid Jason down on the bed. The two lovely ladies made a presentation of stripping each other naked for Jason. He could feel his cock pulsing in his cage. He knew he was leaking, but didn’t care. Diana wiped thenclear fluid from the tip of his cage as Annie turned the lights on low. Diana applied the precum like lip gloss before Annie devoured her lips. Jason groaned into his gag as Annie and Diana were all over each other.  
Annie broke the kiss. “Do you want a repeat of earlier?”  
Jason shook his head. “Nh, mhhnm,” he said through his gag.  
Annie pat him on his head. “Good boy,” she said as Diana sucked on one of her plentiful breasts. Diana had caught Annie by surprise, as was made obvious by the slight moan in her voice.  
Jason watched helplessly as Diana broke the kiss and licked the bridge of his nose, up the length of the dildo protruding from his mouth. He whimpered slightly, wishing that were his cock that Diana was teasing. He watched as Diana teased the head of the dildo, sending Jason’s excitement level through the roof.  
Diana climbed onto the dildo, sliding it right in her wet pussy. As she slid up and down it, Jason was treated to a view of her pussy lips wrapping around the dildo in his mouth. As she fucked it, Jason could smell her juices working overtime. He heard both women moaning quietly, knowing they were kissing.  
Diana’s moaning got louder as she broke the kiss. She was fucking his face faster than before. He felt Annie bouncing on him, almost as if both women were on a sea saw. He watched as Diana stopped on the dildo, he felt her shake on his face. Suddenly, he felt hot juices running down his cheek. He struggled slightly to breathe, and before long, she climbed off his face. She turned around and licked her juices off of him again.  
This time he saw Annie climb off of him, and mount his face. He watched as Annie’s ass took his dildo. She moaned louder as her pussy bounced right onto the tip of his nose. Jason groaned in frustration as Annie’s wetness leaked onto him. Jason couldn’t take it, and before he realized what he was doing, he felt his wrists being untied.  
“You’re enjoying this too much, Princess,” he heard Diana say. Annie held his wrists as Diana climbed onto the bed above his head. Annie passed Jason’s wrists to Diana as she held his hands. “That’s better,” she taunted.  
Annie kept riding Jason’s face, her moans getting louder. Before she knew it, she stopped. Annie mixed her scent with Diana’s as she soaked Jason’s face. 

After Annie came down from her high, she dismounted Jason. As Annie took off the strap on, Diana removed the man’s gag. “I’ll bet you’ve never fully satisfied two women before, have you, Princess,” Diana asked him.  
“No, Miss. I really haven’t,” he answered.  
Annie chimed in. “Maybe we oughta keep him this way: teased, denied, and under lock and key.”  
Diana looked at Jason. “I’ll bet you’d love that, wouldn’t you, puppy?”  
Jason looked at them. “Whatever makes you happy, my ladies.”  
They looked at each other, then Diana looked at Jason. “Strip the bed and start washing the sheets. Miss Annie and I will make the bed. After that, you can sleep in bed with us.”  
Jason smiled. “Yes, Miss Diana!”  
Jason nuzzled into the bed between the two women. All three of them were naked, with Diana on the left, and Annie on the right. The women kissed Jason on the cheeks, before kissing each other good night. Both women turned into Jason, pushing their breasts against him.  
“Turn to Miss Annie,” Diana ordered.  
As if in response, Jason turned to face Annie. She pulled his head into her’s and kissed him. Their tongues explored each other’s mouths. Jason hitched slightly as he felt a finger slide into his ass. He moaned as Diana teased his prostate. Jason didn’t mind, except for the swelling in his cage.  
Annie broke the kiss. “That’s a good boy,” she said to him.  
Before Jason could react, he felt the fingers slide out, and a rubbing on his asshole. He moaned as he felt an object slide into him. Before he turned to look at Diana, he felt an object pull snugly against his hole. Diana had slid his plug inside of him. She kissed him in the same manner as Annie had. “You’ll sleep chaste and plugged. And if there are any accidents, you’ll have more laundry to do,” she told him with a giggle.  
He smiled. “Yes, Miss DiOW!” Annie had reached down and teased his swollen, blue balls before pulling him into her. It didn’t take long for Annie to fall asleep.  
Diana nestled against him, her breasts pressing against his chest. She dozed off peacefully, as had Annie. Jason laid between his two ladies, both in heaven and hell: heaven because he finally pleased two women, yet hell because he didn’t feel a thing except frustration and pain.


	18. Making Adjustments

**Summary for the Chapter:**

> Annie, Diana, and Jason adapt to their new living situation

Jason woke up the next morning, not really aware that he had fallen asleep. He had slept, but didn’t feel rested. He looked around and realized he was in bed alone.  
He jumped up, pulling on the first thing he found, which was a pair of sweatpants, and ran downstairs. What he found surprised him: Diana and Annie were in the kitchen, naked, making a bacon, eggs, and waffle breakfast.  
Annie and Diana looked at him. “Good morning, sunshine,” Annie said.  
Diana looked at him, noting the look of shock and fear on his face. “Your dream! I’m so sorry, I kinda forgot about that,” she said with a hug.  
Jason hugged her back as Annie pulled out the middle chair at the table. “Sit down. Breakfast is almost ready. Diana and I were talking this morning, and we all need to have a sit down.”

Jason looked at the chair, noting it was empty as he sat down. Diana and Annie served up the breakfast they’d prepared and sat down at opposite ends of the table.  
Diana went first. “As you may not know, but have a right to be told, Seth was taken into custody a couple days ago. Apparently, he kidnapped Eva from the convention we went to last month. That was the business in Missouri I had to take care of.  
“For the time being, at least until Annie figures out what’s going on with Seth, she will be staying here with us. Since she’s staying with us, she’s going to be living as we do.” Diana looked at Annie. “What that means is ‘Females come first, followed by males, if at all’. That being said, you’re going to need to fit in.” Diana pointed at Jason. “He’s my Princess, which I will allow you to toy with. However if I feel you’re pushing either his or my limits, I will stop you.” Diana had a flashback to the hotel room, when Eva had them both tied and gagged.  
Annie broke the awkward silence. “I have a question. Are last nights sleeping arrangements typical? Meaning is Princess always going to sleep on the floor, or share the bed?”  
Diana looked at Jason, then at Annie. “Princess usually sleeps in bed with me, chaste and plugged. With that being said, we will need to go bed shopping. That queen size isn’t going to cut it anymore.” She looked at Jason. “Wash last nights sheets after breakfast.”  
When Diana mentioned breakfast, everyone looked down at their plates, as if they’d forgotten about their food. They all dove into their meal, however Jason looked at Diana. “May I ask the pecking order, Miss?”  
Diana looked at him. “Females first, and males second if ever. But, I know what you mean. Your job, Princess, is to please the both of us. However, if I tell you something that contradicts Miss Annie, you will obey me. 50/49/1, me being 50, Annie 49, and you’re the 1. Does that make sense?”  
Jason nodded. “Perfectly, Miss.”  
Diana indicated his plate. “Eat your breakfast, puppy. We have a lot to do today. You’re going to move your stuff into the other bedroom for the time being. At least until after we find out what’s to become of Seth.”  
Jason frowned. “Yes, Miss.”  
“Yes, Miss Diana,” she corrected him.  
“Yes, Miss Diana.” Jason had a realizing his pain and pleasure was about to change.

Jason waited patiently in the car for Diana and Annie outside the furniture store. They were shopping around for a new mattress and box springs. While they were in the car, Jason was instructed to play games on his phone. As he waited, his plug would randomly vibrate at different lengths and intensities. He was glad he was wearing dark shorts today, otherwise he’d be embarrassed. And of course, he’d get random pics from Diana depicting Annie performing random sexual acts. He was getting nauseous from his balls aching so bad.  
Diana and Annie were giggling when they got into the Jeep. “How you feeling, Princess,” Annie taunted as Diana giggles.  
Jason shifted in his seat. “Aching, Miss Annie.”  
Diana climbed on the back of the driver’s seat. “I can fix that when we get home,” she teased.  
Jason grinned. “Thank you, Miss Diana.”  
“Take us to Bed Bath and Beyond, Princess,” Diana instructed.  
Jason nodded. “Yes, Miss Diana,” he said as he started the engine. Jason felt the vibrations die down considerably when he started the engine. No doubt whomever was controlling his plug shut it off.

Jason was walking around Macy’s with Diana while Annie was picking out sheets in Bed Bath and Beyond. Jason was walking funny, and Diana knew why all too well. She took him to the women’s clothing section and grabbed a few outfits. “Help me try these on,” she said.  
Jason grabbed the outfits from her and followed her to the dressing rooms. The clerk ushered them to an empty room. Jason waited for Diana to indicate there were no cameras in the room. He took a quick look around, and dove into the changing room.  
Diana sat him down on the bench. “Sit on your hands, Princess.” Jason placed his hands firmly under his butt and sat down. Diana made a production of taking off her clothes, noting Jason’s crotch started to twitch. “Looks like someone wants some attention,” she teased.  
Jason nodded. “I’m aching so badly right now, Miss Diana!”  
Diana looked at him. “Drop your pants and hold that bench,” she instructed. Jason followed her instructions to the letter. She slid her fingers in her wet pussy before she entered his asshole. She felt him flinch and bare down as she expertly found his prostate. “Would you say you’re at your limit now, Princess?”  
Jason kept his eyes down. “Yes, Miss Diana.”  
Diana gently rubbed his prostate with her finger. She massaged his blue balls with her other hand, causing him to wiggle around. “Keep quiet, or I’ll stop,” she warned him. Jason but his lip as she continued. She could feel his balls fluttering while she rubbed them. Jason couldn’t help but let out a quiet groan.  
Diana gently slid her fingers out of his ass and stop massaging him. “You’ll have to wait until later now,” she said sternly. “Pull your pants back up and get out,” she commanded. Jason did as he was told and waited for Diana to finish what she was doing in the dressing room.

Jason was sitting in the back seat when Annie got to the car. Diana threw her the keys. “Drive,” she instructed. As Annie got in behind the wheel, Diana got in the back seat and sat next to Jason.  
Annie looked in the mirror as Diana took out a roll of black duct tape and started taping Jason to his seat. “Everything ok?”  
Diana slid her pantys off as she looked at Annie. “Princess decided he wanted to wander off on his own while we were at the mall. Go on, Princess. Tell her what you did!”  
Jason looked in the mirror. “I went down to Spencer’s.”  
“Go on,” Diana said as she grabbed one of Jason’s nipples hard enough to twist it off.  
He screamed as she squeezed him. “Miss Diana caught me staring down the clerk’s shirt!”  
Diana showed Annie a picture of the stacked clerk. She was wearing a very low cut top. “So Princess gets to spend the car ride tied to his seat, sucking on my panties,” she said as she stuffed them in his mouth and wrapped tape around his head. She took out a tube of icy hot. “and enduring icy hot for the ride. Take the long way home!”  
Annie started to drive and watched as Diana tore open Jason’s pants and took his package out. He screamed into the gag as she man handled his aching parts. Diana rubbed his balls down with Icy Hot. Jason started grunting and groaning as the icy hot started doing its job.  
Diana noticed Annie wasn’t really taking the long way home. “Pull over. I’ll drive,” she said.  
Annie pulled over and got into the back seat with Jason as Diana drove. Jason watched for the next hour in agony as Diana kept driving past the house. She leaned up to Diana. “Hasn’t he had enough? I want to take a shower and relax. It’s almost 7.”  
Diana looked at the clock. “So it is.” The next time she got to the house, she parked in the garage. When Annie cut Jason free, she left him gagged and his wrists taped behind his back. As Diana led Jason into the house to his special chair, Annie took the bags inside.  
Diana pulled down Jason’s pants before she sat him down on the unlubed dildo and unwrapped Jason’s mouth. “Do you understand why you were punished today?”  
Jason stretched his jaw. “I wandered off in the mall today, and when you found me, I was talking to another woman.”  
Diana looked at him sternly. “What were you two talking about?”  
“She noticed I was walking a little weird, and wanted to make sure I was ok. I spotted she was wearing a key around her ankle, so I started asking some questions, and it turns out she’s a Domme herself,” Jason said. He kept an unwaivering stare at Diana.  
Diana glared at him. “And that’s when I found you?”  
“Yes, Miss Diana.”  
Diana walked over to the sink and soaked up a wash cloth. She returned to Jason and helped him stand up. “Ok, Princess. Lesson here: the big one, don’t wander off! I don’t...” She felt herself choke up a little. She cleared her throat as she washed the icy hot off of his balls. “I don’t think I could stand losing you.” She looked up at him, and noticed he was looking at her. “I said it. I couldn’t stand losing you.”  
Jason waited until she was finished before he knelt. “I love you, Miss Diana.”  
She pulled him into a hug, his head nuzzling her stomach. “I love you too, Jason. Tonight though, for the rest of the night, you’re going to be seen and not heard.” She let go of him and cut his wrists free. “Go get your gag.”

Jason found himself tied on his back to the coffee table, his arms and legs bound to the same leg of the table. He was hooded, gagged, and his chastity device had been removed. He was hard, aching, and he was stark naked.  
Diana and Annie sat back on the couch and sipped their wine as they admired their handiwork. Jason was wiggling, making Annie and Diana very wet. And Jason loved every moment of it!  
Diana stood up and walked over to Jason. “You make a lovely conversation piece, Princess.” She gently stroked his throbbing cock with her fingertips. The slight touch made him flinch and whimper softly. She giggled as Diana sat down and just admired Jason’s figure.  
Annie stood up and walked over to Jason. She slowly started to touch Jason’s throbbing cock with her fingertips. Jason moaned out loud as Annie teased him. “I wish I could let you cum,” she said into his ear.   
Diana watched Annie as she slowly licked him up and down his shaft. Instantly he leaked precum with the touch of her tongue. Jason pulled at his bonds as he moaned loudly. Annie polishes his knob gently, causing him to hitch on the table. “Don’t cum,” Diana instructed. “You’ll be sorry if you do,” she warned him.  
Annie licked his aching balls. Jason groaned in pain and pleasure. Diana ran her hands down her panties and rubbed her clit. She moaned out loud, which caused Jason to groan. “Touch yourself,” Diana told Annie as she motioned for her to come over by Jason’s head.   
Annie walked over to Diana and they touched themselves before Diana took Annie’s hand between her legs. Diana reciprocated, and the two ladies rubbed each other to orgasm. Jason laid on the table, a quivering, leaking mess.


End file.
